Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• , with moderate to excellent enantioselectivity followed by two decarboxylations (Scheme 21). Huang’s group has used azadienes to perform an enantioselective 1,4-addition to afford benzofuran-fused six-membered heterocycles with a squaramide catalyst [56]. Based on their previous work, the authors

• reported an enantioselective 1,4-addition of azadienes 71 to 3-homoacyl coumarins 70 to achieve benzofuran coumarin derivatives 72 [57]. It was possible to obtain good to excellent diastereo- and enantioselectivities by using a low amount of the catalyst, besides the high yield of the reaction. The best

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• high importance in the field of Alzheimer’s disease studies [169]. In 2020, Xu and co-workers described an unprecedented dual C–H functionalization of indolin-2-ones and benzofuran-2-ones via an oxidative C(sp3)–H cross-coupling protocol catalyzed by inexpensive FeCl3 and ligand-free conditions (Scheme

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

• Zhonglie Yang,
• Yutong Liu,
• Kun Cao,
• Xiaobin Zhang,
• Hezhong Jiang and
• Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

• 60 and Umemoto reagent 20 as substrates as well as N-methylmorpholine (NMM) as organic base additive at room temperature (Scheme 21). The highly functionalized indole, pyrrole, benzofuran, and electron-rich benzene containing CF3 can be given in good yield. Given the redox potential of NMM and

All-carbon [3 + 2] cycloaddition in natural product synthesis

• Zhuo Wang and
• Junyang Liu

Beilstein J. Org. Chem. 2020, 16, 3015–3031, doi:10.3762/bjoc.16.251

• rearrangement product 99 in 85% yield. The synthesis of daphenylline (11) was completed by a seven-step synthesis from benzofuran 99. Phosphine-catalyzed enantioselective [3 + 2] annulation In 2019, Lu and co-workers disclosed a novel chiral-phosphine-catalyzed enantioselective [3 + 2] annulation of allenes and

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

• Si-Yuan Liu,
• Xin-Rui Wang,
• Man-Ping Li,
• Wen-Rong Xu and
• Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

• their binding affinities to C60 [25][26][27][28]. Georghiou et al. [29] synthesized the tris(thianthreno)-annelated triquinacene 4, and Cao et al. [30] constructed the tris(naphtho)triquinacene 5, bearing six annelated benzofuran units, and they investigated the supramolecular interaction of these hosts

Reaction of indoles with aromatic fluoromethyl ketones: an efficient synthesis of trifluoromethyl(indolyl)phenylmethanols using K₂CO₃/n-Bu₄PBr in water

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati and
• Gregor Schnakenburg

Beilstein J. Org. Chem. 2020, 16, 778–790, doi:10.3762/bjoc.16.71

• -. 5-, 6-, and 7-azaindoles, 1g–j) provided the corresponding products in the range from 91–97% yield (3u–x). We applied the developed protocol to reactions of other heterocyclic systems such as indazole (4), benzimidazole (5), carbazole (6), benzofuran (7), and benzothiophene (8) with ketone 2a

Recent advances in photocatalyzed reactions using well-defined copper(I) complexes

• Mingbing Zhong,
• Xavier Pannecoucke,
• Philippe Jubault and
• Thomas Poisson

Beilstein J. Org. Chem. 2020, 16, 451–481, doi:10.3762/bjoc.16.42

• ]. Under green light irradiation, a large panel of styrene derivatives was converted into the corresponding α-azidoketones in good to excellent yields. Interestingly, the reaction was extended to the heteroaromatic derivatives, such as thiophene or benzofuran and to β-substituted styrenes. The authors

Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys)

• Ryo Takishima,
• Yuji Nishii,
• Tomoaki Hinoue,
• Yoshitane Imai and
• Masahiro Miura

Beilstein J. Org. Chem. 2020, 16, 325–336, doi:10.3762/bjoc.16.32

• enantiomers in 10–36% yields. The higher yield of 4c was probably due to its better solubility. In order to systematically evaluate the optical properties of these coupling products, a simple benzofuran-fused 1,1’-binaphthyl 6 was also synthesized as a benchmark (Scheme 4). The parent ether 5 was obtained

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

• Soleiman E. Helaly,
• Wilawan Kuephadungphan,
• Patima Phainuphong,
• Mahmoud A. A. Ibrahim,
• Kanoksri Tasanathai,
• Suchada Mongkolsamrit,
• Janet Jennifer Luangsa-ard,
• Souwalak Phongpaichit,
• Vatcharin Rukachaisirikul and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

• presence of a trisubstituted dihydrobenzofuran moiety in 3. COSY and HMBC correlations allowed the construction of a 1,3-pentadiene moiety (C-1′–C-5′), and the linkage to C-2 of the benzofuran ring was determined by a COSY correlation between H-1′ and H-2, as well as HMBC correlations from H-2′ to C-2 and

Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles

• Hoang Huy Do,
• Saif Ullah,
• Alexander Villinger,
• Joanna Lecka,
• Jean Sévigny,
• Peter Ehlers,
• Jamshed Iqbal and
• Peter Langer

Beilstein J. Org. Chem. 2019, 15, 2830–2839, doi:10.3762/bjoc.15.276

• literature procedure, 2,3-dibromobenzofuran (1) was synthesized by bromination of benzofuran [33]. The Suzuki–Miyaura reaction of 1 with 2-bromophenylboronic acid (2), carried out under standard conditions using Pd(PPh3)4, afforded the desired product 3 in 84% yield and with very good regioselectivity. The

• exhibited π–π T-shaped interactions connecting the indole and furan rings with Tyr340. However, π–alkyl linkage was observed between the benzofuran moiety of compound 5c and amino acid Lys295. The fluorine atom of the 4-fluorophenyl group was involved in the binding with the zinc ion and Ser377. Hydrogen

• bonding was found between the oxygen of the benzofuran ring and the hydrogens of Lys291. When compound 6a was docked inside the active pocket of the homology model, it represented π–π stacked and π–alkyl attachment of the indole rings on both sides of the molecule with amino acids His380 and Lys295

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

• Gerardo M. Ojeda,
• Prabhat Ranjan,
• Pavel Fedoseev,
• Lisandra Amable,
• Upendra K. Sharma,
• Daniel G. Rivera and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

• rings, such as furan, benzofuran, pyrrole, benzopyrrole, thiophene, benzothiophene and naphthalene were also successfully synthesized (5d–l) in moderate to very good yields. The exceptions were the cases of indolopyridone 5i and thiazolopyridone 5k, the latter one could not be obtained even after many

Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries

• Xiao Xie,
• Michela Zuffo,
• Marie-Paule Teulade-Fichou and
• Anton Granzhan

Beilstein J. Org. Chem. 2019, 15, 1872–1889, doi:10.3762/bjoc.15.183

• be observed (I/I0 = 40 in the presence of ct DNA and 60 in the presence cl RNA; cf. Figure 6). Conversely, as mentioned above, the dyes containing benzothiophene (1w) or benzofuran (1z, 1þ) residues perform poorly as fluorescent probes. 6) Strongly aggregating dyes (i.e., 1d, 1ð, 10a and 12a

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• character, 2,2,6,6-tetramethyl-1-(1-(2-(4-nitrophenyl)benzofuran-6-yl)ethoxy)piperidine (2a) and its regioisomer 2b, were designed and synthesized. The one-photon (OP) (365 ± 10 nm) and TP (710–760 nm) triggered release (i.e., uncaging) of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical under air

• -responsive photo-labile protecting group [56][57][58] with simple cyclic stilbene structures such as 2-(4-nitrophenyl)benzofuran (NPBF) that absorb in the NIR region of 710–760 nm for the uncaging of bioactive substances such as glutamate and Ca2+ [59][60][61][62][63][64]. Herein, we report the synthesis of

• addition to the fundamental study. Results and Discussion The caged-TEMPOs 2a and 2b were synthesized as shown in Scheme 2. The new compounds, 5-ethyl- and 6-ethyl-2-(4-nitrophenyl)benzofuran (5a and 5b), were synthesized from 1-ethynyl-4-nitrobenzene (4) that was prepared from the commercially available 1

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

• . Similarly, compounds 2–7 were synthesized using different amines including 2-phenylethylamine (for 2), 1-methyltryptamine (for 3), 2-(2-naphthyl)ethylamine hydrochloride (for 4), 2-(1-naphthyl)ethylamine hydrochloride (for 5), 2-(1H-inden-3-yl)ethylamine hydrobromide (for 6) [21], and 2-(1-benzofuran-3-yl

Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source

• Tetsuaki Fujihara and
• Yasushi Tsuji

Beilstein J. Org. Chem. 2018, 14, 2435–2460, doi:10.3762/bjoc.14.221

• in good TON. Benzofuran (32h) and indole (32i) also gave the carboxylic acids, which were isolated as their methyl esters. Li and co-workers reported the Rh-catalyzed site-selective C(sp2)–H carboxylation reaction using 2-arylphenols as the substrates (Scheme 31) [62]. The desired reactions proceeded

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• conjugates form layer-like structures during crystal formation via multiple hydrogen bonding interactions. This structural information indeed helps to design novel MGBs with much better binding affinity and specificity. A new family of conjugates between a Zn(II)-tach complex and (indole)2 or benzofuran

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

• ) in 52% yield. For 3-aryl-2-propynoic acids bearing heteroaromatic groups, treatment of 3-(benzothiophen-2’-yl)-2-propynoic acid (1n) and 3-(benzofuran-2’-yl)-2-propynoic acid (1o) under the same procedure and conditions gave the corresponding coumarins 3An and 3Ao in moderate yields, respectively

Fluorogenic PNA probes

• Tirayut Vilaivan

Beilstein J. Org. Chem. 2018, 14, 253–281, doi:10.3762/bjoc.14.17

• derivative. 5-Benzothiophene- and 5-benzofuran-modified uracil in aegPNA exhibited a fluorescence that was marginally sensitive to the environment [195]. When incorporated into PNA, benzothiophene-uracil exhibited an increased fluorescence compared to the free nucleoside. The opposite effect was observed

• with benzofuran-uracil, and the fluorescence was almost completely quenched when G was the flanking nucleobase. Significant fluorescence enhancement with a small blue-shift of the emission maxima was observed upon duplex formation with DNA for both modified uracil derivatives. Unfortunately, the

• discrimination between complementary and mismatched duplex observed with benzothiophene-uracil was limited to sequences with flanking Cs. No discrimination was observed with benzofuran-uracil PNA unless it was used in combination with GO as a quencher for ssPNA [196]. In this respect, the thiophene-modified

Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds

• Alexey Yu. Dubovtsev,
• Maksim V. Dmitriev,
• Аndrey N. Maslivets and
• Michael Rubin

Beilstein J. Org. Chem. 2017, 13, 2179–2185, doi:10.3762/bjoc.13.218

• ; spiro compounds; synthetic methods; Introduction Molecular structures based on partially or exhaustively hydrogenated indole and benzofuran cores are omnipresent in nature. Both types of ring systems are found in a variety of important biologically active natural products [1][2][3][4][5][6][7][8][9][10

• in the target-oriented synthesis of pyrrole-based natural alkaloids [34][35][36][37][38]. Herein we wish to report a new synthetic route towards spirocyclic scaffolds possessing partially hydrogenated indole or benzofuran cores. The featured approach is based on the highly efficient regiodivergent

Synthesis of novel 13α-estrone derivatives by Sonogashira coupling as potential 17β-HSD1 inhibitors

• Ildikó Bacsa,
• Rebeka Jójárt,
• János Wölfling,
• Gyula Schneider,
• Bianka Edina Herman,
• Mihály Szécsi and
• Erzsébet Mernyák

Beilstein J. Org. Chem. 2017, 13, 1303–1309, doi:10.3762/bjoc.13.126

• 17β-HSD1 inhibitors, displaying submicromolar IC50 values. Keywords: benzofuran; 13α-estrone; 17β-HSD1 inhibition; partial saturation; Sonogashira coupling; Introduction Synthetic modifications of the naturally occurring female prehormone estrone may lead to compounds with diverse biological

• , suppressing the conversion by less than 15%. The phenylalkynyl derivatives in the 3-OMe series 9a–e and 11a–e exerted weak inhibitions. Phenylalkenyl compounds 13 and 15 and benzofuran compounds 12 and 14 displayed weaker inhibitory activity than their alkynyl counterparts 8c and 10c. The full saturation

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

• Adrián A. Heredia and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2017, 13, 910–918, doi:10.3762/bjoc.13.92

• halides. Successive reaction with terminal alkynes in the presence of t-BuOK affords the corresponding alkyl alkynyl selenide in moderate to good yields. Finally, this methodology allowed the synthesis of 2-alkylselanyl-substituted benzofuran and indole derivatives starting from convenient 2-substituted

• -pot synthesis of heterocycles derived from indole and benzofuran, convenient ortho-substituted phenylacetylenes were also tested. To our delight, the o-diethylamino-substituted derivative 6i afforded N-ethyl-2-(n-octylselanyl)-1H-indole (9) in 62% isolated yield (Scheme 4). The primary selenyl

• (Table 4, entry 10). The subsequent electrophilic addition of I2 to selenide 5q afforded 3-iodo-2-(n-octylselanyl)benzofuran (10) in excellent yield (93% isolated yield, Scheme 4). Finally, we compared our method with syntheses reported in the literature that mainly rely on commercially available

Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G

• Youngeun Jung,
• Dileep Kumar Singh and
• Ikyon Kim

Beilstein J. Org. Chem. 2016, 12, 2689–2693, doi:10.3762/bjoc.12.266

• Youngeun Jung Dileep Kumar Singh Ikyon Kim College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon 21983, Republic of Korea 10.3762/bjoc.12.266 Abstract The recognition of the local symmetric image within benzofuran-based

• in the literature [4][5][6][7][8][9][10]. In connection with our research on benzofurans [11][12], our laboratory has been involved in the synthesis of these benzofuran-containing natural products for the last several years [13][14][15]. For example, we have reported a concise total synthesis of

• (Scheme 5) [43][44]. Conclusion In summary, we have established a highly scalable and flexible synthetic route to several benzofuran-containing oligostilbenoid natural products by relying on a symmetry-breaking strategy from 3,5-dimethoxybenzyl alcohol. The relative reactivity of ester, aldehyde, and

A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

• John Andraos

Beilstein J. Org. Chem. 2016, 12, 2420–2442, doi:10.3762/bjoc.12.236

• target bond 3-partition dissection maps for 27 commonly found heterocyclic rings is given in the Supporting Information File 1 (see Schemes S6 to S32). These include benzimidazole, 2,3-dihydro-1H-benzo[b][1,4]diazepine, benzofuran, benzopyran, chromen-4-one, coumarin, cyclopent-2-enone, furan, Hantzsch

Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis

• Maddali L. N. Rao,
• Jalindar B. Talode and
• Venneti N. Murty

Beilstein J. Org. Chem. 2016, 12, 2065–2076, doi:10.3762/bjoc.12.195

• : bromobenzofuran coupling; cross-coupling; palladium; regio-selective; triarylbismuth; Introduction The benzofuran scaffold is present in various biologically active molecules [1][2][3][4][5][6][7][8], natural products [9][10][11][12][13][14][15] and also part of various functional materials [16]. Importantly

• expected to attract easy applications in structural elaborations of medicinally important benzofuran scaffolds. Important benzofuran skeletons. X-ray structure of bis-coupling product 3.1 (CCDC-1425338) [43]. Bis- and tris-couplings. Screening for mono-arylation.a Cross-couplings of 2,3-dibromobenzofurans