Ga(OTf)3-promoted condensation reactions for 1,5-benzodiazepines and 1,5-benzothiazepines

Xiang Qiang Pan; Jian Ping Zou; Zhi Hao Huang; Wei Zhang

doi:10.1016/j.tetlet.2008.06.082

Ga(OTf)₃-promoted condensation reactions for 1,5-benzodiazepines and 1,5-benzothiazepines

Xiang Qiang Pan
, Jian Ping Zou
, Zhi Hao Huang
, Wei Zhang

Chemistry

Soochow University

Research output: Contribution to journal › Article › peer-review

Abstract

Condensation reactions of o-phenylenediamine and two equivalents of acetophenone under gallium(III) triflate catalysis produce biaryl-substituted 1,5-benzodiazepines. Similar reactions of o-phenylenediamine or o-aminothiophenol and o-hydroxy chalcones lead to formation of functionalized 1,5-benzodiazepines and 1,5-benzothiazepines in good to excellent yields. The ortho-hydoxy group of chalcones is crucial for this unprecedented condensation process.

Original language	English
Pages (from-to)	5302-5308
Number of pages	7
Journal	Tetrahedron Letters
Volume	49
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2008.06.082
State	Published - Sep 1 2008

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.06.082

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title = "Ga(OTf)3-promoted condensation reactions for 1,5-benzodiazepines and 1,5-benzothiazepines",

abstract = "Condensation reactions of o-phenylenediamine and two equivalents of acetophenone under gallium(III) triflate catalysis produce biaryl-substituted 1,5-benzodiazepines. Similar reactions of o-phenylenediamine or o-aminothiophenol and o-hydroxy chalcones lead to formation of functionalized 1,5-benzodiazepines and 1,5-benzothiazepines in good to excellent yields. The ortho-hydoxy group of chalcones is crucial for this unprecedented condensation process.",

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T1 - Ga(OTf)3-promoted condensation reactions for 1,5-benzodiazepines and 1,5-benzothiazepines

AU - Pan, Xiang Qiang

AU - Zou, Jian Ping

AU - Huang, Zhi Hao

AU - Zhang, Wei

PY - 2008/9/1

Y1 - 2008/9/1

N2 - Condensation reactions of o-phenylenediamine and two equivalents of acetophenone under gallium(III) triflate catalysis produce biaryl-substituted 1,5-benzodiazepines. Similar reactions of o-phenylenediamine or o-aminothiophenol and o-hydroxy chalcones lead to formation of functionalized 1,5-benzodiazepines and 1,5-benzothiazepines in good to excellent yields. The ortho-hydoxy group of chalcones is crucial for this unprecedented condensation process.

AB - Condensation reactions of o-phenylenediamine and two equivalents of acetophenone under gallium(III) triflate catalysis produce biaryl-substituted 1,5-benzodiazepines. Similar reactions of o-phenylenediamine or o-aminothiophenol and o-hydroxy chalcones lead to formation of functionalized 1,5-benzodiazepines and 1,5-benzothiazepines in good to excellent yields. The ortho-hydoxy group of chalcones is crucial for this unprecedented condensation process.

UR - https://www.scopus.com/pages/publications/47549116710

UR - https://www.scopus.com/pages/publications/47549116710#tab=citedBy

U2 - 10.1016/j.tetlet.2008.06.082

DO - 10.1016/j.tetlet.2008.06.082

M3 - Article

AN - SCOPUS:47549116710

SN - 0040-4039

VL - 49

SP - 5302

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

Ga(OTf)₃-promoted condensation reactions for 1,5-benzodiazepines and 1,5-benzothiazepines

Abstract

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