NaH promoted [4+3] annulation of crotonate-derived sulfur ylides with thioaurones: synthesis of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines-Reference-Cited by-同舟云学术

NaH promoted [4+3] annulation of crotonate-derived sulfur ylides with thioaurones: synthesis of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines

Published:2017 Issue:77 Volume:53 Page:10672-10675
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Zhang Youquan¹²³⁴⁵,Yu Aimin¹²³⁴⁵,Jia Jiru¹²³⁴⁵,Ma Shanshan¹²³⁴⁵,Li Ke¹²³⁴⁵,Wei Yin⁶⁷⁸⁹¹⁰^ORCID,Meng Xiangtai¹²³⁴⁵^ORCID

Affiliation:

1. Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion

2. School of Chemistry & Chemical Engineering

3. Tianjin University of Technology

4. Tianjin 300384

5. P. R. China

6. State Key Laboratory of Organometallic Chemistry

7. University of Chinese Academy of Sciences

8. Shanghai Institute of Organic Chemistry

9. Chinese Academy of Sciences

10. Shanghai 200032

Abstract

The [4+3] annulation reaction of crotonic acid derivative sulfur ylides with thioaurones has, for the first time, been reported using NaH as the base. A diverse array of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines is obtained in good to excellent yields. The proposed mechanism is investigated and supported by DFT calculations.

Funder

National Natural Science Foundation of China

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2017/CC/C7CC04466F

Reference37 articles.

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2. A Novel Chiral Sulfonium Yilde: Highly Enantioselective Synthesis of Vinylcyclopropanes

3. Stereocontrolled Aziridination of Imines via a Sulfonium Ylide Route and a Mechanistic Study

4. A Convenient Synthesis of Chiral Nonracemic Vinyl Aziridines

5. Direct synthesis of chiral aziridines from N-tert-butyl-sulfinylketimines

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