Synthesis of Multi-substituted Benzo[b]thiophene-4-ol Derivatives by Organobase-driven

doi:10.6023/cjoc202508019

Chinese Journal of Organic Chemistry

ARTICLE

有机碱驱动合成多取代苯并[b]噻吩-4-醇类化合物

任传清^*, 李欣欣, 郭家伟, 季晓晖, 刘波

陕西理工大学化学与环境科学学院陕西省催化基础与应用重点实验室陕西汉中 723000

收稿日期:2025-11-23 修回日期:2026-01-03
基金资助:
国家自然科学基金项目(No.22101165)和陕西省教育厅重点实验室项目(No. 23JS002)资助.

Synthesis of Multi-substituted Benzo[b]thiophene-4-ol Derivatives by Organobase-driven

Ren Chuanqing^*, Li Xinxin, Guo Jiawei, Ji Xiaohui, Liu Bo

Shaanxi Key laboratory of Catalysis, School of Chemical & Environmental Science, Shaanxi University of Technology, Han-zhong, Shaanxi 723000

Received:2025-11-23 Revised:2026-01-03
Contact: ^*E-mail: rcqing2008@126.com
Supported by:
National Natural Science Foundation of China(No. 22101165) and the Project of the Key Laboratory of Education Department of Shaanxi Province (No. 23JS002).

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Abstract

Multi-substituted benzo[b]thiophene skeleton is an important synthetic intermediate. In this paper, a series of Multi-substituted benzo[b]thiophene-4-ol derivatives were successfully constructed from 3-substituted group-1-(thiophen-3-yl)prop-2-en-1-one and nitroso compound via Organobase-driven cycloaddition reactions. Optimization experiments showed that the best experimental conditions were as follows: using DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) (2.5 mmol) as base,the 3-substituted group-1-(thiophen-3-yl)prop-2-en-1-one (1.0 mmol) and nitroso compound (1.2 mmol) reacted at r.t. for 8 h in DMF(N,N-Dimethylformamide), Multi-substituted Benzo[b]thiophene-4-ol derivatives were synthesized with a yield of 88%. The composition and structure has been characterized by¹H NMR,¹³C NMR and HR-MS(ESI). The mechanism for the reaction was proposed in this paper. The menthod has the characteristics of mild conditions and practical efficiency.

Key words: organobase-driven, benzo[b]thiophene, synthesis

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Ren Chuanqing, Li Xinxin, Guo Jiawei, Ji Xiaohui, Liu Bo. Synthesis of Multi-substituted Benzo[b]thiophene-4-ol Derivatives by Organobase-driven[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202508019.

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有机碱驱动合成多取代苯并[b]噻吩-4-醇类化合物

Synthesis of Multi-substituted Benzo[b]thiophene-4-ol Derivatives by Organobase-driven

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