Article
Chemistry, Multidisciplinary
Jiali Huang, Wenyang Wang, Lei Zhang, Xiangtai Meng
Summary: This review summarizes the latest developments in the construction of benzo[b]thiophene-fused heterocycles by ring formation at the C2-C3-position of benzo[b]thiophene derivatives in the past decade. The review is divided into four parts according to the four kinds of benzo[b]thiophene derivatives used, including thioaurone, thioisatin, substituted benzo[b]thiophene, and azadiene.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Linting Di, Jie Yang, Weiguo Tang, Lizhi Gai, Zhikuan Zhou, Hua Lu
Summary: The addition of sufficient-electron heterocycle rings to the BODIPY core resulted in red or near infrared emission. The synthesis of nonsymmetric benzo[a]fused and thiophene/thieno[3,2-b]thiophene[b]fused BODIPY derivatives with a reactive site allowed for the development of new compounds through nucleophilic substitution reactions. X-ray crystallographic analysis revealed a planar core structure with pi-pi interactions, and changes in absorption and emission were rationalized through density functional theory calculations.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Jingyu Zhang, Wei Xia, Saskia Huda, Jas S. Ward, Kari Rissanen, Markus Albrecht
Summary: A copper(II)-catalyzed dearomative cyclization amination of N-(2-aminobenzoyl) indoles is described, yielding tetracyclic indolines under mild conditions with good yields. Tetracyclic 5a,6-dihydroindolo[2,1-b]quinazolin-12(5H)-ones are obtained in good to excellent yields (up to 99% yield) by N-Ts bond cleavage using trifluoromethanesulfonic acid (TfOH) mediation. The resulting compounds can be easily functionalized through simple synthetic methods.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Subramani Kumaran, Kanniyappan Parthasarathy
Summary: An efficient Rh(III)-catalyzed cross-dehydrogenative coupling of N-pyridinylindoles with benzo[b]thiophene 1,1-dioxides has been developed via directing-group-assisted C-H activation, forming a new C-C bond from two inert C-H bonds in a one-pot reaction. The synthesized compounds exhibit compatibility with various functional groups and their emission properties have been explored.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Evgeny B. Ulyankin, Anastasia S. Kostyuchenko, Sergey A. Chernenko, Mikhail O. Bystrushkin, Anna L. Samsonenko, Anton L. Shatsauskas, Alexander S. Fisyuk
Summary: A new approach based on iodine-promoted photocyclization was developed for the synthesis of fused benzothiophene derivatives, providing an efficient method compared to traditional oxidative coupling and palladium-catalyzed intramolecular arylation. This method allows for the synthesis of a variety of functionally substituted fused heterocycles containing pyridine and carbazole moieties.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Firdoos Ahmad Sofi, Mubashir H. Masoodi, Mohammad Ovais Dar, Prasad V. Bharatam
Summary: Copper(I) catalysed oxidative conversion of imidazopyridines into N-pyridinylamides has been achieved via tandem C-C and C-N bond cleavages under oxidative reaction conditions. The methodology has wide substrate scope and products were formed in good to excellent yields. This method is suitable for the oxidative conversion of both C-3 functionalized as well as non-functionalized imidazopyridines.
Article
Chemistry, Organic
Shyamal Pramanik, Partha Pratim Mondal, Soumitra Maity
Summary: In this study, a simple strategy for the C-H alkylation of electron-rich (hetero)arenes with alkyl bromides was disclosed, using visible-light-mediated organo-photocatalytic SET processes. The method showed generality with different alkyl radicals and electron-rich arenes under mild conditions. The addition of Zn(OAc)2 as a bromide scavenger controlled the extent of alkylation with alkyl bromides and prevented the formation of potential bromo-arene byproducts. Furthermore, a sequential C-H alkylation strategy for selective bis-alkylation was developed efficiently.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Plant Sciences
Sachika Hirazawa, Yohei Saito, Momoko Sagano, Masuo Goto, Kyoko Nakagawa-Goto
Summary: Natural products with enzymatic synthesis have a wide range of biological activities. Our study focuses on the antiproliferative activity of novel benzo[b]thiophenyl (BT) flavones, which have a 10 pi-electron BT ring B instead of the usual 6 pi-electron phenyl ring. We synthesized and evaluated 10 isoflavones, 29 chalcones, and 4 aurones, and found that certain BT-flavonoids displayed significant antiproliferative effects against human tumor cell lines. Furthermore, our studies demonstrate the importance of BT instead of phenyl as ring B for the isoflavone and chalcone derivatives.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Chemistry, Organic
Qifu Lin, Wen Yang, Yongqi Yao, Yue Li, Lin Wang, Dingqiao Yang
Summary: A novel copper-catalyzed cycloaddition reaction has been developed for the synthesis of 2,3-dihydrobenzo[b]thiophene derivatives from diaryl disulfides and heterobicyclic alkenes. This reaction demonstrates excellent diastereoselectivity and a broad substrate scope, with various functional groups tolerated on the substrates to yield the corresponding exo adducts in moderate yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Deepa Rawat, Subbarayappa Adimurthy
Summary: The ruthenium-catalyzed reaction and the metal-free reaction proceed through different intermediates, indicating distinct mechanisms for the transformations. Control experiments suggest that both reactions follow the ionic mechanism.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Sawsan H. Alelaiwi, James R. Mckee
Summary: A direct and effective method for synthesizing primary amine of several polycyclic aromatic compounds through copper (I)-catalyzed Ullmann C-N coupling is reported. This method also allows the synthesis of new N-substituted dibenzothiophene derivatives. The use of inexpensive catalysts and aqueous ammonia as the ammonia source makes this protocol environmentally and economically advantageous.
Article
Chemistry, Organic
Victorino Vallejos Gonzalez, Justin Kahle, Christopher Huessler, Robin Heckershoff, A. Stephen K. Hashmi, Bernhard Birenheide, Adrian Hauser, Joachim Podlech
Summary: This paper describes the synthesis of three penta- and three hexahelicenes containing two terminal thiophene units. The syntheses of pentahelicenes involved the 1,4-bisalkynylation of a benzene precursor and double Suzuki coupling in the 2,3-position to introduce thiophene units. The ortho,ortho' fusion yielding the final products was achieved with catalysts such as platinum(II) chloride or JohnPhos-complexed gold(I). A similar approach was used for the synthesis of hexahelicenes, starting with a naphthalene derivative and involving 2,7-bisalkynylation and subsequent double Suzuki coupling. The ortho,ortho' fusion to the respective hexahelicenes was achieved using platinum(II) chloride or, preferably, indium(III) chloride. UV/Vis spectra and cyclic voltammograms were recorded, and HOMO/LUMO gaps were calculated using DFT methods for all helicenes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ming-Zhong Guo, Mei-Jin Mou, Zhuo Chen, Shao-Fei Ni, Ming Li, Li-Rong Wen, Lin-Bao Zhang
Summary: A straightforward electrochemical reduction of benzo[b]thiophene 1,1-dioxides with HFIP as the hydrogen donor has been reported. The study demonstrated the tolerance of various functional groups and the potential applications of this methodology through scaled-up experiments.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Agriculture, Multidisciplinary
Desheng Zhang, Jian Zhang, Ting Liu, Shang Wu, Zengxue Wu, Sikai Wu, Runjiang Song, Baoan Song
Summary: The evolution of insect resistance has made it difficult for traditional insecticides to control the bean aphid. To address this issue, a new series of compounds were designed and synthesized, which showed moderate to outstanding insecticidal activity against the bean aphid. Compound L14 exhibited significant insecticidal activity and inhibited ATPase. Additionally, it was found that L14 might act on the central nervous system of aphids and interact with nicotinic acetylcholine receptors.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2022)
Article
Chemistry, Organic
Bharti Yadav, Prosenjit Isar, Mangalampalli Ravikanth
Summary: A variety of fused benzo-benzisapphyrins were synthesized by reacting benzodipyrrole-derived diol and para-benzitripyrrane in the presence of TFA and DDQ. The structure and properties of the fused sapphyrins were characterized using HRMS, 1D and 2D NMR spectroscopy.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
