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Search for "microwave irradiation" in Full Text gives 242 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Steroid diversification by multicomponent reactions

  • Leslie Reguera,
  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

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  • with a thiosemicarbazide and 2-bromo-1-phenylethan-1-one under microwave irradiation to form the steroid–thiazole hybrid 35 in very good yield. As previously mentioned, due to the poor reactivity of steroidal ketones and their imine derivatives, most MCRs with ketosteroids described in the literature
  • required a high temperature set by classic heating or microwave irradiation. Using cholic acid as carboxylic acid component, Cui and co-workers [37] developed a novel MCR resembling the Ugi-4CR, but relying on the reactivity of ynamides as surrogates of the isocyanide component. Ynamides are alkynes with a
  • strong oxidizing Jones reagent, because the oxidizing power of sulfuric acid was not enough to achieve oxidation. Interestingly, the use of microwave irradiation instead of classic heating allowed obtaining the Biginelli product in only 10 min, instead of 12 h as required for the synthesis of pyrimidines
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Published 06 Jun 2019

Extending mechanochemical porphyrin synthesis to bulkier aromatics: tetramesitylporphyrin

  • Qiwen Su and
  • Tamara D. Hamilton

Beilstein J. Org. Chem. 2019, 15, 1149–1153, doi:10.3762/bjoc.15.111

Graphical Abstract
  • -solvent-added routes to porphyrins, including high-temperature sealed-bomb methods [15][16][17], gas-phase synthesis [9], and microwave irradiation [10] do not employ a second oxidation step. Presumably for the latter two methods open to air, dioxygen serves as a rapid oxidizer under high-temperature
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Published 22 May 2019

Switchable selectivity in Pd-catalyzed [3 + 2] annulations of γ-oxy-2-cycloalkenones with 3-oxoglutarates: C–C/C–C vs C–C/O–C bond formation

  • Yang Liu,
  • Julie Oble and
  • Giovanni Poli

Beilstein J. Org. Chem. 2019, 15, 1107–1115, doi:10.3762/bjoc.15.107

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  • . Using DMF and DMA as solvents at 130 °C (Table 1, entries 10 and 11), and [Pd(η3-C3H5)Cl]2, dppf] as the catalytic system in DMSO (Table 1, entry 12) did not allow further improvements for the formation of compound 5a. Furthermore, after 1 h at 130 °C under microwave irradiation, the desired compound 5a
  • at 130 °C, 6 h (conditions B), or 1 h under microwave irradiation (conditions C)]. Scope The scope of the C–C/O–C [3 + 2] annulation between dimethyl 3-oxoglutarate (1a) and six- (2a), five- (2b) and seven-membered (2c) cyclic α,β-unsaturated-γ-oxycarbonyls was next studied (Scheme 3). Under the
  • thermal conditions or microwave irradiation. Surprisingly, application of these protocols to the seven-membered bis-electrophile 2c led to the corresponding bicyclo[5.3.0]decane-3,9-dione (5c) with a low yield of 24% under thermal conditions B, while microwave irradiation was ineffective. Moderate yields
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Published 16 May 2019

Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions

  • Angélica de Fátima S. Barreto and
  • Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2019, 15, 906–930, doi:10.3762/bjoc.15.88

Graphical Abstract
  • four consecutive IMCRs were employed. The strategy allowed the synthesis of a cyclic heptapeptoid in only 8 steps using microwave irradiation in seven of these steps allowing short reaction times (3–5 minutes) and excellent yields of the intermediates (88–98%). The non-optimized low yield of the last
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Published 15 Apr 2019

Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors

  • Kirill B. Polyanskii,
  • Kseniia A. Alekseeva,
  • Pavel V. Raspertov,
  • Pavel A. Kumandin,
  • Eugeniya V. Nikitina,
  • Atash V. Gurbanov and
  • Fedor I. Zubkov

Beilstein J. Org. Chem. 2019, 15, 769–779, doi:10.3762/bjoc.15.73

Graphical Abstract
  • ) by a reaction of 2-(2-bromoethyl)benzyl bromide with secondary amines under microwave irradiation followed by the decomposition of the products under the action of potassium tert-butoxide [46]. All of the above routes offer some advantages but they all are rather expensive. Thus, the initial stage of
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Published 22 Mar 2019

Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

  • Iteng Ng-Choi,
  • Àngel Oliveras,
  • Lidia Feliu and
  • Marta Planas

Beilstein J. Org. Chem. 2019, 15, 761–768, doi:10.3762/bjoc.15.72

Graphical Abstract
  • degassed 1,2-dimethoxyethane (DME)/EtOH/H2O (9:9:2) under microwave irradiation at 120 °C for 30 min (Scheme 2). An aliquot of the resulting resin 5 was cleaved, and HPLC and mass spectrometry analysis of the crude reaction mixture revealed the formation of the biaryl cyclic peptide 6 in 18% purity. Mass
  • to an intramolecular Suzuki–Miyaura reaction using Pd2(dba)3 (0.2 equiv), SPhos (0.4 equiv) and KF (4 equiv) in degassed DME/EtOH/H2O (9:9:2) under microwave irradiation at 120 ºC for 30 min. Mass spectrometry analysis of the crude reaction mixture from the cleavage of an aliquot of the resulting
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Published 22 Mar 2019

Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks

  • Clémence Moitessier,
  • Ahmad Rifai,
  • Pierre-Edouard Danjou,
  • Isabelle Mallard and
  • Francine Cazier-Dennin

Beilstein J. Org. Chem. 2019, 15, 721–726, doi:10.3762/bjoc.15.67

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  • -dimethylformamide system was tested according to the study of Fang et al. [25] revealing that the methoxy group in the meta-position of an electron-withdrawing substituents can be removed under microwave irradiation. However, when testing the system on 5b, no reaction occurred. Another experiment with lithium
  • ) in the presence of different Brønsted acids. While investigating these conditions in combination with microwave irradiation (Scheme 4), the desired compound 4-HO-OPA (6) was successfully obtained in only 30 minutes, with a good yield (75%) when reacting with methanesulfonic acid (MsOH) as catalyst
  • compound 5b (200 mg, 1.2 mmol), p-TsOH (1.68g, 9.8 mmol) and [Bmim]Br (4.0 g, 18.3 mmol) was placed in a sealed vial and irradiated under microwave irradiation for 30 minutes at 150 °C under strong agitation. After cooling, the mixture was vigorously extracted with Et2O overnight. The ether layer was
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Published 19 Mar 2019

Synthesis and SAR of the antistaphylococcal natural product nematophin from Xenorhabdus nematophila

  • Frank Wesche,
  • Hélène Adihou,
  • Thomas A. Wichelhaus and
  • Helge B. Bode

Beilstein J. Org. Chem. 2019, 15, 535–541, doi:10.3762/bjoc.15.47

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  • bond formation was achieved using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl), 1-hydroxybenzotriazole (HOBt) and N,N-diisopropylethylamine (DIPEA) in DMF under microwave irradiation (Scheme 1). Racemic 1 was synthesized using tryptamine and (rac)-3-methyl-2-oxopentanoic acid
  • phthalimides 16 and 23 [29]. These intermediary compounds 16 and 23 also allowed an N-methylation of the azaindole moiety with sodium hydride (NaH) and methyl iodide (MeI) to yield 17 and 24. By ethanolic hydrazinolysis and microwave irradiation the phthalimides (16, 17, 23, and 24) were deprotected yielding
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Published 25 Feb 2019

Design of indole- and MCR-based macrocycles as p53-MDM2 antagonists

  • Constantinos G. Neochoritis,
  • Maryam Kazemi Miraki,
  • Eman M. M. Abdelraheem,
  • Ewa Surmiak,
  • Tryfon Zarganes-Tzitzikas,
  • Beata Łabuzek,
  • Tad A. Holak and
  • Alexander Dömling

Beilstein J. Org. Chem. 2019, 15, 513–520, doi:10.3762/bjoc.15.45

Graphical Abstract
  • optimization, we improved the Ugi-macrocyclization procedure compared to our previous findings utilizing microwave irradiation (see Supporting Information File 1); Firstly, the corresponding amino acid was irradiated with indole-3-carboxaldehyde derivatives 6 using MeOH as solvent (5 mL) at 120 °C for 1 h
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Published 20 Feb 2019

Ammonium-tagged ruthenium-based catalysts for olefin metathesis in aqueous media under ultrasound and microwave irradiation

  • Łukasz Gułajski,
  • Andrzej Tracz,
  • Katarzyna Urbaniak,
  • Stefan J. Czarnocki,
  • Michał Bieniek and
  • Tomasz K. Olszewski

Beilstein J. Org. Chem. 2019, 15, 160–166, doi:10.3762/bjoc.15.16

Graphical Abstract
  • to the classical conditions. On the other hand, microwave irradiation turned out to be less effective leading to a drop in the reaction yield for 1a (48%) and a slightly increased yield in the case of 4b (55%). In the homometathesis reaction of allyl alcohol 8 (Table 1, entries 3 and 4) both
  • is in agreement with the known fact that in protic solvents ruthenium hydrides are formed leading to isomerisation byproducts [66]. Finally, we were pleased to see that the use of ultrasound or microwave irradiation were beneficial for the CM of alcohol 8 with methyl acrylate (10, Table 1, entries 5
  • justifying the use of modified catalysts. For the ammonium NHC-tagged catalysts (0.25 mol %), the use of microwave irradiation was more productive than ultrasound treatment. This effect was most pronounced in the case of catalysts with low solubility in water such as 1b or the insoluble catalysts 1d and 2c
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Published 17 Jan 2019

Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins

  • Christiane Schultze and
  • Bernd Schmidt

Beilstein J. Org. Chem. 2018, 14, 2991–2998, doi:10.3762/bjoc.14.278

Graphical Abstract
  • the past few years. Starting materials are allyl ethers of salicylic aldehydes or ketones 5 and the stable ylide ethyl (triphosphoranylidene)acetate (6), which upon microwave irradiation undergo a tandem Claisen rearrangement/Wittig olefination/cyclization sequence. This sequence was pioneered by the
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Published 05 Dec 2018

Pd-Catalyzed microwave-assisted synthesis of phosphonated 13α-estrones as potential OATP2B1, 17β-HSD1 and/or STS inhibitors

  • Rebeka Jójárt,
  • Szabolcs Pécsy,
  • György Keglevich,
  • Mihály Szécsi,
  • Réka Rigó,
  • Csilla Özvegy-Laczka,
  • Gábor Kecskeméti and
  • Erzsébet Mernyák

Beilstein J. Org. Chem. 2018, 14, 2838–2845, doi:10.3762/bjoc.14.262

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  • reacted with diethyl phosphite or diphenylphosphine oxide using Pd(PPh3)4 as catalyst under microwave irradiation. The influence of the new compounds on the transport function of the organic anion transporting polypeptide OATP2B1 was investigated by measuring Cascade Blue uptake. Derivatives bearing a 3
  • . Here we disclose the synthesis of novel 2- or 4-substituted 13α-estrone derivatives 8–13 via the Hirao reaction (Scheme 1). Diethyl phosphite (7a) or diphenylphosphine oxide (7b) were chosen as >P(O)H reagents and C–P couplings were planned under microwave irradiation using Pd-based catalysis
  • , but the important benefits of microwave-irradiation have also been utilized in this field [29]. The optimization of reaction conditions was carried out using 2-bromo- or 2-iodo-13α-estrone 3-methyl ether (1 or 1I) as starting compounds and diethyl phosphite (7a) as the reagent (Table 1, Scheme 1). Two
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Published 14 Nov 2018
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  • polyhydroquinoline derivatives 118 under microwave irradiation. Several substituted aldehydes 7 with dimedone (20), acetoacetate ester 34a, and ammonium acetate in ethanol under microwave irradiation were reacted to produce corresponding products in high yields. In addition to the catalytic role of strong acid
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Published 01 Nov 2018

Synthesis of dihydroquinazolines from 2-aminobenzylamine: N3-aryl derivatives with electron-withdrawing groups

  • Nadia Gruber,
  • Jimena E. Díaz and
  • Liliana R. Orelli

Beilstein J. Org. Chem. 2018, 14, 2510–2519, doi:10.3762/bjoc.14.227

Graphical Abstract
  • -aryl-2-iminoazacycloalkanes [84] and 2-oxazolines or their higher homologues [85], using polyphosphoric acid esters PPE (ethyl polyphosphate) [86] and PPSE (trimethylsilyl polyphosphate) [87] under microwave irradiation. PPE and PPSE are aprotic irreversible dehydrating agents of the Lewis acid-type
  • esters are their low cost, operational simplicity and minimum environmental impact. Besides, their use together with microwave irradiation brings about shorter reaction times, cleaner crude products and consequently higher yields. On the basis of our previous work on DHQs [41], we explore herein the use
  • latter [85][88]. Additionally, the classical work-up procedure of PPSE-promoted reactions involves basic conditions [85]. In fact, treatment of 3b with PPSE/Cl2CH2 under microwave irradiation afforded the desired product 1b with 90% yield (Table 3). In a control experiment, 3b was reacted with PPE/Cl3CH
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Published 26 Sep 2018

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

  • Sambasivarao Kotha,
  • Milind Meshram and
  • Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

Graphical Abstract
  • , Claisen rearrangement (CR) of 77 under microwave irradiation (MWI) conditions on a silica gel support followed by O-allylation of the resulting CR product furnished diallyl compound 78. Treatment of diallyl compound 78 with G-I catalyst 1 delivered the expected naphthoxepine derivative 79 (96%). Next
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Published 21 Sep 2018

Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide

  • Lu Yang,
  • Yuwei Wu,
  • Yiming Yang,
  • Chengping Wen and
  • Jie-Ping Wan

Beilstein J. Org. Chem. 2018, 14, 2348–2353, doi:10.3762/bjoc.14.210

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  • synthesis of N-substituted 1,2,3-triazoles via the reactions of organoazides and the in situ prepared N,N-dimethylenaminones by 150 °C microwave irradiation and subsequent heating in toluene at 100 °C, providing an effective protocol of enaminone-based 1,2,3-triazole synthesis. Interestingly, our continuous
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Published 07 Sep 2018

Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines

  • Itaru Nakamura,
  • Mao Owada,
  • Takeru Jo and
  • Masahiro Terada

Beilstein J. Org. Chem. 2018, 14, 1972–1979, doi:10.3762/bjoc.14.172

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  • and alkoxylcarbonyloxy groups generally require long heating times at elevated reaction temperatures (>140 °C) or microwave irradiation (Scheme 2a). In contrast, N-sulfonyloxyanilines are known to readily undergo the [3,3]-rearrangement during the preparation of the starting material below −20 °C due
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Published 31 Jul 2018

β-Hydroxy sulfides and their syntheses

  • Mokgethwa B. Marakalala,
  • Edwin M. Mmutlane and
  • Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

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  • catalyst loading required as well as recoverability and reusability without any significant loss of activity in terms of reaction time, selectivity and yield. For reactions that are sluggish and mostly require heating, microwave irradiation is reported to significantly improve reaction rates, selectivities
  • electron rich ones such as p-methylthiophenol, giving the corresponding products in very high yields. Unlike in the microwave irradiation protocol, the reaction of aliphatic thiols with epoxides proceeded smoothly to give excellent yields. In another contribution, Su et al. carried out thiolysis of
  • oxidation to β-hydroxy sulfoxides under microwave irradiation. Gallium triflate-catalyzed ring opening of epoxides and one-pot oxidation. Thiolysis of epoxides and one-pot oxidation to β-hydroxy sulfoxides using Ga(OTf)3 as a catalyst. Ring opening of epoxide using ionic liquids under solvent-free
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Published 05 Jul 2018

Synthesis of pyrazolopyrimidinones using a “one-pot” approach under microwave irradiation

  • Mark Kelada,
  • John M. D. Walsh,
  • Robert W. Devine,
  • Patrick McArdle and
  • John C. Stephens

Beilstein J. Org. Chem. 2018, 14, 1222–1228, doi:10.3762/bjoc.14.104

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  • reaction conditions were chosen to match the already developed microwave-assisted synthesis of the 5-aminopyrazoles. A solution of the β-ketonitrile in methanol was treated with hydrazine and heated to 150 °C under microwave irradiation for 5 min. The β-ketoester and acetic acid were then simply added to
  • the pot and the reaction heated at the same temperature, 150 °C, under microwave irradiation for a further 2 h. The target pyrazolo[1,5-a]pyrimidinone was subsequently isolated in an overall yield of 52%. Once more, a significant improvement was observed using microwave conditions in comparison with
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Published 28 May 2018

The first Pd-catalyzed Buchwald–Hartwig aminations at C-2 or C-4 in the estrone series

  • Ildikó Bacsa,
  • Dávid Szemerédi,
  • János Wölfling,
  • Gyula Schneider,
  • Lilla Fekete and
  • Erzsébet Mernyák

Beilstein J. Org. Chem. 2018, 14, 998–1003, doi:10.3762/bjoc.14.85

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  • A facile Pd-catalyzed C(sp2)–N coupling to provide a range of 2- or 4-[(subst.)phenyl]amino-13α-estrone derivatives has been achieved under microwave irradiation. The reactions were mediated with the use of Pd(OAc)2 as a catalyst and KOt-Bu as a base in the presence of X-Phos as a ligand. The
  • (dba)3 as catalysts, X-Phos as a ligand, Cs2CO3 as a base in toluene or DMF solvent under thermal heating or microwave irradiation [18]. We recently described halogenations [19] and Sonogashira couplings on ring A of 13α-estrone and its 3-methyl ether [20]. The 13-epimer of natural estrone is a non
  • -estrone 3-methyl ethers are also effective inhibitors [19]. Recently, we carried out the Pd-catalyzed C–C coupling of 2- and 4-iodo-13α-estrones as well as their 3-methyl ethers with p-substituted phenylacetylenes as terminal alkyne partners under microwave irradiation [20]. The regioisomerism markedly
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Published 04 May 2018

Mannich base-connected syntheses mediated by ortho-quinone methides

  • Petra Barta,
  • Ferenc Fülöp and
  • István Szatmári

Beilstein J. Org. Chem. 2018, 14, 560–575, doi:10.3762/bjoc.14.43

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  • as catalysts. These latest strategies provide efficient syntheses under mild conditions without using harsh chemicals. Furthermore, the application of microwave irradiation or sonication is also preferred to conventional heating methods to accelerate the reactions. Synthesis of aminoalkylphenols The
  • were also formed in around 90% yields under microwave irradiation (Scheme 7). Miscellaneous reactions It is also known that o-QMs could cross-link two biologically important molecules such as peptides, proteins or nucleic bases. (see section Biological properties) Achieving the reaction under
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Published 06 Mar 2018

Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: possible route to the 4-methylpregabalin core structure

  • Denisa Vargová,
  • Rastislav Baran and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2018, 14, 553–559, doi:10.3762/bjoc.14.42

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  • . This transformation is perhaps similar to acetal hydrolysis in neat water under microwave irradiation [41]. Because of this efficient process, compound 11 was isolated in one synthetic operation in 80% yield from amine 9. In the last step, precursor 11 reacted with either amine (R,R)-12 or (S,S)-12, to
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Published 05 Mar 2018

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8

  • Teppei Sasaki,
  • Katsuhiko Moriyama and
  • Hideo Togo

Beilstein J. Org. Chem. 2018, 14, 345–353, doi:10.3762/bjoc.14.22

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  • -ketoesters and phenols (the Pechmann condensation) [17]. Recent studies for the metal-catalyzed reactions for the synthesis of the coumarin skeleton are as follows: the Yb(OTf)3-catalyzed microwave irradiation of phenols and propynoic acids [18], the Pd(OAc)2-catalyzed oxidative cyclocarbonylation of 2
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Published 05 Feb 2018

Continuous-flow retro-Diels–Alder reaction: an efficient method for the preparation of pyrimidinone derivatives

  • Imane Nekkaa,
  • Márta Palkó,
  • István M. Mándity and
  • Ferenc Fülöp

Beilstein J. Org. Chem. 2018, 14, 318–324, doi:10.3762/bjoc.14.20

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  • ] syntheses of heterocyclic compounds. The rDA products can be gained, due to a thermal [4 + 2]-cycloreversion, by distillation under reduced pressure [29], boiling in solvent [30][31], and applying microwave irradiation [32][33][34][35] or flash vacuum pyrolysis [35][36]. rDA reactions under mild conditions
  • of our results, tricyclic 15b was also prepared alternately: the mixture of 3-aminobicyclo[2.2.2]oct-5-ene-carboxylic acid, triethylorthoformate, aniline and acetic acid was subjected to microwave irradiation at 120 W at 80 °C for 20 min. After completion of the reaction, as monitored by TLC, 20
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Published 01 Feb 2018

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

  • Ranjana Aggarwal and
  • Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

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  • ). Interestingly, high yields of the corresponding pyrazolo[3,4-b]pyridines 34 were obtained when reactions were carried under solvent-free microwave irradiation. The synthesized pyrazolo[3,4-b]pyridines have shown potential cytotoxic activity against cervical HeLa and prostate DU 205 cancer cell lines. A similar
  • reaction of 5-aminopyrazole 16, isatin 54 and 3-oxo-3-phenylpropanenitriles 15 in acetic acid under microwave irradiation at 80 °C in just 20 minutes (Scheme 14). Hao et al. [62] described the unexpected synthesis of naphthoic acid substituted pyrazolo[3,4-b]pyridine derivatives 70 via a three-component
  • domino reaction of 5-aminopyrazoles 16, cyclic 1,3-diones 58 and arylglyoxals 98 under microwave irradiation. Triethylamine (20 mol %) as base and DMSO as solvent at 120 °C provided best results with high yields of pyrazolo[3,4-e]indolizines (a derivative of pyrazolo[3,4-b]pyridines) 102 (Scheme 30
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Published 25 Jan 2018
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