Base-Controlled Divergent Synthesis of Fluorine-Containing Benzo[4,5]imidazo[2,1‑b][1,3]thiazines from 2‑Mercaptobenzimidazoles and β‑CF3‑1,3-Enynes

Base-Controlled Divergent Synthesis of Fluorine-Containing Benzo[4,5]imidazo[2,1‑b][1,3]thiazines from 2‑Mercaptobenzimidazoles and β‑CF3‑1,3-Enynes

A base-controlled divergent cyclization between 2-mercaptobenzimidazoles and β-CF3-1,3-enynes providing either trifluoromethylated or fluorinated benzo­[4,5]­imidazo­[2,1-b]­[1,3]­thiazines has been developed. The β-CF3-1,3-enyne, as a three-carbon synthon, underwent a 1,8-diazabicyclo[5.4.0] undec-...

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Veröffentlicht in:Journal of organic chemistry 2023-09, Vol.88 (18), p.13262-13271
Hauptverfasser: He, Zhi-Qing, Chen, Shu-Jie, Chen, Guo-Shu, Lin, Jin-Hao, Wu, Jia-Ming, Liu, Yun-Lin
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container_end_page 13271
container_issue 18
container_start_page 13262
container_title Journal of organic chemistry
container_volume 88
creator He, Zhi-Qing
Chen, Shu-Jie
Chen, Guo-Shu
Lin, Jin-Hao
Wu, Jia-Ming
Liu, Yun-Lin
description A base-controlled divergent cyclization between 2-mercaptobenzimidazoles and β-CF3-1,3-enynes providing either trifluoromethylated or fluorinated benzo­[4,5]­imidazo­[2,1-b]­[1,3]­thiazines has been developed. The β-CF3-1,3-enyne, as a three-carbon synthon, underwent a 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU)-catalyzed tandem hydroamination/intramolecular hydrothiolation to give CF3-substituted 3,4-dihydro-2H-benzo­[4,5]­imidazo­[2,1-b]­[1,3]­thiazine, whereas reaction with KOH afforded fluorinated 4H-benzo­[4,5]­imidazo­[2,1-b]­[1,3]­thiazine exclusively. In addition, the synthetic utility of this methodology was showcased through a variety of downstream derivatizations.
doi_str_mv 10.1021/acs.joc.3c01570
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title Base-Controlled Divergent Synthesis of Fluorine-Containing Benzo[4,5]imidazo[2,1‑b][1,3]thiazines from 2‑Mercaptobenzimidazoles and β‑CF3‑1,3-Enynes
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