Electrophilic Cyclization of o-Anisole- and o-Thioanisole-Substituted Ynamides­: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes

Yulong Kong; Lian Yu; Lingzi Fu; Jian Cao; Guoqiao Lai; Yuming Cui; Ziqiang Hu; Guanhai Wang

doi:10.1055/s-0033-1338481

Synthesis, Table of Contents

Synthesis 2013; 45(14): 1975-1982
DOI: 10.1055/s-0033-1338481

paper

Electrophilic Cyclization of o-Anisole- and o-Thioanisole-Substituted Ynamides: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes

Yulong Kong

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 Email: caojian@hznu.edu.cn

,

Lian Yu

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 Email: caojian@hznu.edu.cn

,

Lingzi Fu

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 Email: caojian@hznu.edu.cn

,

Jian Cao*

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 Email: caojian@hznu.edu.cn

,

Guoqiao Lai

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 Email: caojian@hznu.edu.cn

,

Yuming Cui

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 Email: caojian@hznu.edu.cn

,

Ziqiang Hu

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 Email: caojian@hznu.edu.cn

,

Guanhai Wang

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 Email: caojian@hznu.edu.cn

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Abstract

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Abstract

A facile synthesis of 3-substituted 2-amidobenzofurans and 2-amidobenzothiophenes via electrophilic cyclization reaction of o-anisole- and o-thioanisole-substituted ynamides with I₂, NBS and NCS was developed. The products 3-iodo-2-amidobenzofurans were further transferred into 3-aryl-, 3-alkynyl, and 3-vinyl-2-amidobenzofurans via Pd-catalyzed reactions such as Suzuki–Miyaura and Sonogashira cross-coupling reactions and the Heck reaction.

Key words

2-amidobenzofurans - 2-amidobenzothiophenes - electrophilic cyclization - ynamide - cross-coupling reaction

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References

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Supplementary Material

Supporting Information

Electrophilic Cyclization of o-Anisole- and o-Thioanisole-Substituted Ynamides­: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes

Electrophilic Cyclization of o-Anisole- and o-Thioanisole-Substituted Ynamides: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes