Construction of 2‑Arylbenzo[4,5]thieno[2,3‑d]thiazole Skeleton via CuCl/S-Mediated Three-Component Reaction

An exclusive thiophene-fused polycyclic π-conjugated 2-arylbenzo­[4,5]­thieno­[2,3-d]­thiazole skeleton was constructed via a one-pot CuCl-mediated three-component reaction, using 2-(2-bromophenyl)­acetonitrile and aromatic aldehydes as substrates and elemental sulfur as sulfur source in the presenc...

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Bibliographic Details
Published in:Organic letters 2020-01, Vol.22 (2), p.448-452
Main Authors: Zhang, Wei, Tao, Shanqing, Ge, Huaibin, Li, Qiao, Ai, Zhenkang, Li, Xiaoxian, Zhang, Beibei, Sun, Fengxia, Xu, Xiaqing, Du, Yunfei
Format: Article
Language:English
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Summary:An exclusive thiophene-fused polycyclic π-conjugated 2-arylbenzo­[4,5]­thieno­[2,3-d]­thiazole skeleton was constructed via a one-pot CuCl-mediated three-component reaction, using 2-(2-bromophenyl)­acetonitrile and aromatic aldehydes as substrates and elemental sulfur as sulfur source in the presence of K2CO3 and 1,10-phen in DMSO. A plausible reaction mechanism was proposed, which involved formation of benzo­[b]­thiophen-2-amines through cyclization of 2-bromophenyl acetonitrile and sulfur, and subsequent intramolecular condensation/dehydrogenation with aromatic aldehydes.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04206