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Search for "one-pot reaction" in Full Text gives 176 result(s) in Beilstein Journal of Organic Chemistry.

One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular SN2 reaction

  • Yiwen Xiong,
  • Ping Qian,
  • Chenhui Cao,
  • Haibo Mei,
  • Jianlin Han,
  • Guigen Li and
  • Yi Pan

Beilstein J. Org. Chem. 2014, 10, 1802–1807, doi:10.3762/bjoc.10.189

Graphical Abstract
  • . Herein, we report an anomalous outcome in the one-pot reaction, which provides a highly efficient method for the synthesis of α,β-differentiated diamino esters directly from readily available starting materials, α,β-unsaturated ester, N,N-dichlorotoluenesulfonamide (TsNCl2) and benzylamine. Furthermore
  • benzylamine under similar reaction conditions of the third step of this one-pot reaction (Scheme 3). To our delight, aziridine 6 was converted into the corresponding diamino acid ester 5b with 73% chemical yield. Thus, aziridine most likely might be the intermediate in this reaction. Based on the above
  • results, a proposed reaction mechanism for this one-pot reaction is illustrated in Scheme 4, which contains the sequence of aminochlorination, aziridination and followed by the SN2 nucleophilic ring-opening. The first step is the Cu-catalyzed aminochlorination reaction of methyl cinnamate 1a resulting in
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Published 07 Aug 2014

Design and synthesis of multivalent neoglycoconjugates by click conjugations

  • Feiqing Ding,
  • Li Ji,
  • Ronny William,
  • Hua Chai and
  • Xue-Wei Liu

Beilstein J. Org. Chem. 2014, 10, 1325–1332, doi:10.3762/bjoc.10.134

Graphical Abstract
  • -allohexopyranoside (2a) in gram scale via BF3∙OEt2-promoted one-pot three-component α-selective tandem hydroamination/glycosylation reaction (Scheme 1). In fact, when 3,4,6-tri-O-acetyl-D-glucal (1a), propargyl alcohol and p-toluenesulfonamide were subjected to a one-pot reaction in the presence of 2.2 equiv of BF3
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Published 10 Jun 2014

The Ugi four-component reaction as a concise modular synthetic tool for photo-induced electron transfer donor-anthraquinone dyads

  • Sarah Bay,
  • Gamall Makhloufi,
  • Christoph Janiak and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 1006–1016, doi:10.3762/bjoc.10.100

Graphical Abstract
  • spectroscopy [56]. The donor-only (2) and acceptor-only (3) models for spectroscopic comparison were obtained analogously. For enabling rapid accesses to functional π-systems, such as Do–Acc dyads for photo-induced charge separation, besides a robust, flexible diversity-oriented one-pot reaction, such as the
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Published 05 May 2014

Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins

  • G. Gangadhararao,
  • Ramesh Kotikalapudi,
  • M. Nagarjuna Reddy and
  • K. C. Kumara Swamy

Beilstein J. Org. Chem. 2014, 10, 996–1005, doi:10.3762/bjoc.10.99

Graphical Abstract
  • the nitrogen lone pair on the β-carbon [24] of the allene forming addition product II or III. This upon treating with aq NaOH leads to the deacylated/debenzoylated phosphinoylindoles. In the one-pot reaction, though, the in situ generated allenylphosphine oxide first undergoes deacylation
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Published 02 May 2014

Convergent synthesis of a tetrasaccharide repeating unit of the O-specific polysaccharide from the cell wall lipopolysaccharide of Azospirillum brasilense strain Sp7

  • Pintu Kumar Mandal,
  • Debashis Dhara and
  • Anup Kumar Misra

Beilstein J. Org. Chem. 2014, 10, 293–299, doi:10.3762/bjoc.10.26

Graphical Abstract
  • 1. A number of suitably functionalized monosaccharide intermediates 2, 3 [30], 4 [31], and 5 [32] were prepared from the reducing sugars by using literature reports. The application of a one-pot reaction sequence for the stereoselective glycosylation and the removal of the p-methoxybenzyl (PMB
  • “armed–disarmed” effect as well as the removal of PMB ether in a one-pot reaction following the glycosylation reduced the overall number of steps. Experimental General methods All reactions were monitored by thin-layer chromatography over silica gel-coated TLC plates. TLC spots were visualized by warming
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Published 29 Jan 2014

Substrate dependent reaction channels of the Wolff–Kishner reduction reaction: A theoretical study

  • Shinichi Yamabe,
  • Guixiang Zeng,
  • Wei Guan and
  • Shigeyoshi Sakaki

Beilstein J. Org. Chem. 2014, 10, 259–270, doi:10.3762/bjoc.10.21

Graphical Abstract
  • convenient method of the W-K reduction [4][5]. The method involves heating R1(R2)C=O, KOH and hydrazine hydrate (H2N–NH2·H2O) together in diethylene glycol (DEG in Scheme 1). This method gives the products from steroid ketones in a one-pot reaction and with a high yield. Scheme 2 shows the reaction mechanism
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Published 23 Jan 2014

Organobase-catalyzed three-component reactions for the synthesis of 4H-2-aminopyrans, condensed pyrans and polysubstituted benzenes

  • Moustafa Sherief Moustafa,
  • Saleh Mohammed Al-Mousawi,
  • Maghraby Ali Selim,
  • Ahmed Mohamed Mosallam and
  • Mohamed Hilmy Elnagdi

Beilstein J. Org. Chem. 2014, 10, 141–149, doi:10.3762/bjoc.10.11

Graphical Abstract
  • generated using a one-pot reaction involving condensation of ethyl propiolate (4a) with benzylidenemalononitrile (7a) in the presence of L-proline (5) (Scheme 4) [4]. It is believed that the pathway followed in this process involves conjugate addition of proline to the propiolate to yield adduct 6 which
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Published 14 Jan 2014

Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate

  • Hong Gao,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 2934–2939, doi:10.3762/bjoc.9.330

Graphical Abstract
  • functionalized 2-pyrrolidinon-3-olates 2a–2h as a one-pot reaction: A mixture of 2-aminobenzothiazole (2.0 mmol), acetylenedicarboxylate (2.0 mmol), aromatic aldehyde (2.0 mmol), morpholine or piperidine (3.0 mmol) and p-toluenesulfonic acid (0.5 mmol) in ethanol (10.0 mL) was stirred at room temperature for
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Published 27 Dec 2013

One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

  • Santos Fustero,
  • Paula Bello,
  • Javier Miró,
  • María Sánchez-Roselló,
  • Günter Haufe and
  • Carlos del Pozo

Beilstein J. Org. Chem. 2013, 9, 2688–2695, doi:10.3762/bjoc.9.305

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  • group, which involved the use of 1,7-octadiene as an internal source of ethylene. Keywords: cross metathesis; Diels–Alder; one-pot reaction; organo-fluorine; propargylic difluorides; Introduction In recent years the number of applications of olefin metathesis as a mild and competitive synthetic method
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Published 28 Nov 2013

One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction

  • Diego Carnaroglio,
  • Katia Martina,
  • Giovanni Palmisano,
  • Andrea Penoni,
  • Claudia Domini and
  • Giancarlo Cravotto

Beilstein J. Org. Chem. 2013, 9, 2378–2386, doi:10.3762/bjoc.9.274

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  • : isocyanates; microwave-assisted reaction; one-pot reaction; tandem Staudinger–aza-Wittig reaction; urea derivatives; Introduction The industrial and commercial impact of isocyanates (R–NCO) is steadily growing. In particular, the polyurethane output has undergone yearly increases of 5% over the last decade
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Published 06 Nov 2013

Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

  • Sudipta Pathak,
  • Kamalesh Debnath and
  • Animesh Pramanik

Beilstein J. Org. Chem. 2013, 9, 2344–2353, doi:10.3762/bjoc.9.269

Graphical Abstract
  • ninhydrin to form Schiff bases. To overcome the above problems we have designed an operationally simple one-pot reaction for the synthesis of pyrrole-fused isocoumarins (5 or 8) from the ninhydrin adducts of acetylacetone/ethyl acetoacetate (6 or 7) [43] and primary amines 2 under solvent-free conditions
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Published 04 Nov 2013

AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds

  • Qiuping Ding,
  • Dan Wang,
  • Puying Luo,
  • Meiling Liu,
  • Shouzhi Pu and
  • Liyun Zhou

Beilstein J. Org. Chem. 2013, 9, 1949–1956, doi:10.3762/bjoc.9.231

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  • single operation, play an important role in atom-economical organic chemistry. A cascade reaction is the most efficient way for targeting fine chemicals, agrochemicals, pharmaceutical drugs, drug intermediates and ingredients by a one-pot reaction in environmentally and economically friendly synthetic
  • regioselective alkylation of isoquinoline N-oxide and its derivatives with sulfoxides for the synthesis of 1-alkylated isoquinolines [40]. We also reported the synthesis of 1-arylated 1,3-disubstituted isoquinoline N-oxides in a one-pot reaction characterized by a Ag-catalyzed intramolecular addition cyclization
  • -alkenylated isoquinoline 4 was synthesized via a Pd-mediated C–H bond activation approach in a one-pot reaction. The intermediate isoquinoline N-oxide A was produced in situ from 2-alkynylbenzaldoximes and reacted with the α,β-unsaturated carbonyl compound 2e to yield 1-alkenylated isoquinoline 4 (Scheme 3
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Published 27 Sep 2013

Synthesis of enones, pyrazolines and pyrrolines with gem-difluoroalkyl side chains

  • Assaad Nasr El Dine,
  • Ali Khalaf,
  • Danielle Grée,
  • Olivier Tasseau,
  • Fares Fares,
  • Nada Jaber,
  • Philippe Lesot,
  • Ali Hachem and
  • René Grée

Beilstein J. Org. Chem. 2013, 9, 1943–1948, doi:10.3762/bjoc.9.230

Graphical Abstract
  •  3). It appeared that the reaction conditions for the synthesis of these pyrazolines were compatible with the first isomerisation step, therefore the possibility of a "one-pot" reaction was considered. Indeed, by heating a mixture of propargylic alcohols 2a–2e with DBU (1,8-diazabicycloundec-7-ene
  • ) in the presence of methylhydrazine (Scheme 4) the pyrazolines 4a–4e were obtained after 3–7 h in excellent yields (82–92%, Table 2). This very short and efficient synthesis of pyrazolines 4 can be related to another excellent one-pot reaction with 3-components where the first step is a Pd-catalyzed
  • Supporting Information File 1 for details). The reaction conditions were compatible with both steps and an example of a one-pot reaction was performed starting from 2a–2e. The desired pyrrolines 6a–6e were obtained in excellent yields (71–76%, Scheme 6 and Table 3). Another important issue was the
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Published 26 Sep 2013

Straightforward synthesis of a tetrasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O16

  • Manas Jana and
  • Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 1757–1762, doi:10.3762/bjoc.9.203

Graphical Abstract
  • stereoselective glycosylation of compounds 2 and 3 in the presence of a combination of N-iodosuccinimide (NIS) and triflic acid (TfOH) [18][19], followed by the removal of the p-methoxybenzyl (PMB) group in a one-pot reaction [17] by tuning the reaction conditions furnished the disaccharide acceptor 6 in 76
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Published 28 Aug 2013

Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

  • Tamashree Ghosh,
  • Abhishek Santra and
  • Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 974–982, doi:10.3762/bjoc.9.112

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  • carbonotrithioate (derived from the reaction of CS2 and Na2S·9H2O) furnished thioglycosides and glycosyl thiols in excellent yield with high stereoselectivity in a two-step, one-pot reaction condition. The reaction condition is operationally simple, mild, reproducible, high-yielding, highly stereoselective, and can
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Published 22 May 2013

Synthesis of functionalized spiro[indoline-3,4’-pyridines] and spiro[indoline-3,4’-pyridinones] via one-pot four-component reactions

  • Li-Juan Zhang,
  • Qun Wu,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 846–851, doi:10.3762/bjoc.9.97

Graphical Abstract
  • arylamines and other primary amines. Keywords: 1,4-dihydropyridine; electron-deficient alkyne; four-component reaction; isatin; one-pot reaction; spiro compound; Introduction β-Enaminones and β-enamino esters represent important synthetic building blocks for the development of versatile carbon–carbon bond
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Published 02 May 2013

A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions

  • Murugan Sathishkumar,
  • Sangaraiah Nagarajan,
  • Poovan Shanmugavelan,
  • Murugan Dinesh and
  • Alagusundaram Ponnuswamy

Beilstein J. Org. Chem. 2013, 9, 689–697, doi:10.3762/bjoc.9.78

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  • are presented below. Results and Discussion At the outset, optimization of the one-pot reaction was attempted by varying the solvents and using triethylamine as the acid scavenger (Table 1). The reaction was also attempted under solvent-free conditions. The latter was more promising in the sense that
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Published 10 Apr 2013

1-n-Butyl-3-methylimidazolium-2-carboxylate: a versatile precatalyst for the ring-opening polymerization of ε-caprolactone and rac-lactide under solvent-free conditions

  • Astrid Hoppe,
  • Faten Sadaka,
  • Claire-Hélène Brachais,
  • Gilles Boni,
  • Jean-Pierre Couvercelle and
  • Laurent Plasseraud

Beilstein J. Org. Chem. 2013, 9, 647–654, doi:10.3762/bjoc.9.73

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  • . In this quest and encouraged by our previous results, we chose to explore the potential of zwitterionic 1-n-butyl-3-methylimidazolium-2-carboxylate (BMIM-2-CO2, Figure 1). Indeed, methylimidazolium-2-carboxylates can be easily synthesized with high yields by the one-pot reaction of dimethyl carbonate
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Published 03 Apr 2013

Reactions of salicylaldehyde and enolates or their equivalents: versatile synthetic routes to chromane derivatives

  • Ishmael B. Masesane and
  • Zelalem Yibralign Desta

Beilstein J. Org. Chem. 2012, 8, 2166–2175, doi:10.3762/bjoc.8.244

Graphical Abstract
  • used. Chromane derivatives from the reactions of salicylaldehyde and enolate equivalents derived from malononitrile and its derivatives The one-pot reaction of salicylaldehyde and malononitrile has proved to be an efficient method for the synthesis of 2-iminochromene derivatives. In general such
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Published 12 Dec 2012

An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives

  • Wentao Gao,
  • Guihai Lin,
  • Yang Li,
  • Xiyue Tao,
  • Rui Liu and
  • Lianjie Sun

Beilstein J. Org. Chem. 2012, 8, 1849–1857, doi:10.3762/bjoc.8.213

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  • -aminobenzophenone (1) with 4-chloroethylacetoacetate by using CAN (cerium ammonium nitrate, 10 mol %) as catalyst at room temperature. The substrates 3a–l were prepared through one-pot reaction of ethyl 2-(chloromethyl)-4-phenylquinoline-3-carboxylate (2) and substituted phenols. Our developed strategy, involving a
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Published 30 Oct 2012

Copper-catalyzed CuAAC/intramolecular C–H arylation sequence: Synthesis of annulated 1,2,3-triazoles

  • Rajkumar Jeyachandran,
  • Harish Kumar Potukuchi and
  • Lutz Ackermann

Beilstein J. Org. Chem. 2012, 8, 1771–1777, doi:10.3762/bjoc.8.202

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  • Rutjes [68] as well as Sharpless [69] elegantly devised alternative approaches exploiting 1-haloalkynes [70], we became interested in exploring a single [71][72][73] inexpensive copper catalyst for one-pot reaction sequences comprising a 1,3-dipolar cycloaddition along with an intramolecular C–H bond
  • catalytic efficacy. Subsequently, we explored the extension of this approach to the development of a chemoselective three-component one-pot reaction. Thus, we found that alkyl bromides 2 could be directly employed as user-friendly substrates for the in situ formation of the corresponding organic azides
  • (Scheme 3). Notably, the catalytic system proved broadly applicable, and a variety of organic electrophiles 2, thereby, delivered differently decorated N-substituted 1,4-dihydrochromeno[3,4-d][1,2,3]triazoles 4. Importantly, performing the one-pot reaction in a sequential fashion was not found to be
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Published 16 Oct 2012

Enantioselective total synthesis of (R)-(−)-complanine

  • Krystal A. D. Kamanos and
  • Jonathan M. Withey

Beilstein J. Org. Chem. 2012, 8, 1695–1699, doi:10.3762/bjoc.8.192

Graphical Abstract
  • turned to its conversion to amino alcohol 4. It was envisioned that such conversion could be effected in a one-pot reaction by employing lithium aluminium hydride reduction of an aldoximine [5], formed in situ by condensation of a suitably oxygenated aldehyde 5 with hydroxylamine hydrochloride (Scheme 3
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Published 04 Oct 2012

Asymmetric one-pot sequential Friedel–Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme

  • Kengo Akagawa,
  • Ryota Umezawa and
  • Kazuaki Kudo

Beilstein J. Org. Chem. 2012, 8, 1333–1337, doi:10.3762/bjoc.8.152

Graphical Abstract
  • -functionalized indole or pyrrole derivatives in a highly enantioselective manner. Keywords: Friedel–Crafts-type alkylation; laccase; one-pot reaction; organocatalysis; α-oxyamination; resin-supported peptide catalyst; Findings Indole derivatives represent a class of biologically active compounds [1][2][3], and
  • followed by oxygenation at the α-position of the carbonyl group. If such a sequence can be realized in a one-pot reaction, it would be a powerful method for the synthesis of oxy-functionalized indole derivatives with operational simplicity. To date, there has been no report on the FCAA reaction combined
  • oxyamination, even though indoles are generally prone to be oxidized [39][40]. By considering that enzymes promote reactions efficiently under aqueous conditions, we thought it necessary to conduct the one-pot reaction in aqueous media. Therefore, the reaction sequence shown in Table 1 was first examined in
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Published 17 Aug 2012

Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition

  • Kazato Inanaga,
  • Yu Ogawa,
  • Yuuki Nagamoto,
  • Akihiro Daigaku,
  • Hidetoshi Tokuyama,
  • Yoshiji Takemoto and
  • Kiyosei Takasu

Beilstein J. Org. Chem. 2012, 8, 658–661, doi:10.3762/bjoc.8.73

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  • sequence, Tf2NH catalyzes both of the reactions. Keywords: isomerization; one-pot reaction; organocatalysis; silyl enol ethers; triflic imide; Introduction Silyl enol ethers, which are isolable equivalents of metal enolates, are useful and important intermediates in synthetic chemistry [1][2][3]. They
  • ) cycloaddition of silyl enol ethers with acrylates generating substituted cyclobutanes [10]. We are intrigued that the isomerization of silyl enol ethers and successive (2 + 2) cycloaddition could be promoted by Tf2NH in a one-pot reaction. When 1a was treated with Tf2NH (1 mol %) under the isomerization
  • silyl enol ethers. Kinetically favourable silyl enol ethers were smoothly converted into thermodynamically stable ones by treatment with a catalytic amount of Tf2NH under mild conditions. Moreover, we demonstrated that the one-pot reaction involves two different catalytic reactions, an isomerization and
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Published 27 Apr 2012

Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles

  • Pavol Jakubec,
  • Dane M. Cockfield,
  • Madeleine Helliwell,
  • James Raftery and
  • Darren J. Dixon

Beilstein J. Org. Chem. 2012, 8, 567–578, doi:10.3762/bjoc.8.64

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  • /bjoc.8.64 Abstract A versatile nitro-Mannich/lactamisation cascade for the direct stereoselective synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles has been developed. A highly enantioenriched substituted 5-nitropiperidin-2-one was synthesised in a four component one-pot
  • reaction combining an enantioselective organocatalytic Michael addition with the diastereoselective nitro-Mannich/lactamisation cascade. Protodenitration and chemoselective reductive manipulation of the heterocycles was used to install contiguous and fully substituted stereocentres in the synthesis of
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Published 16 Apr 2012
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