Annulated 1,2,4-triazoles. A convenient synthesis of thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines: A novel triheterocyclic ring system

Quanrui Wang; Zheng Li; Haiyan Yang; Feng Li; Zongbiao Ding; Fenggang Tao

doi:10.1055/s-2003-39392

Annulated 1,2,4-triazoles. A convenient synthesis of thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines: A novel triheterocyclic ring system

Quanrui Wang, Zheng Li, Haiyan Yang, Feng Li, Zongbiao Ding, Fenggang Tao

Houston Methodist

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

18 Scopus citations

Abstract

A synthetic approach to the previously unknown thieno[2,3-f][1,2,4]triazolo[1,5-a]azepine derivatives was efficiently accomplished by cycloaddition of the bicyclic 1-aza-2-azoniaallene salts 6, derived from 6,7-dihydrobenzo[b]thiophen-4(5H)-one hydrazones 4, to the triple bond of nitriles, followed by ring enlargement. The X-ray crystal diffraction analysis of the picrate 10a provided affirmative proof for the structural assignment made.

Original language	English (US)
Pages (from-to)	1231-1235
Number of pages	5
Journal	Synthesis
Issue number	8
DOIs	https://doi.org/10.1055/s-2003-39392
State	Published - 2003

Keywords

1-aza-2-azoniaallene cations
Cycloaddition
Nitriles
Ring enlargement
Thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2003-39392

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title = "Annulated 1,2,4-triazoles. A convenient synthesis of thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines: A novel triheterocyclic ring system",

abstract = "A synthetic approach to the previously unknown thieno[2,3-f][1,2,4]triazolo[1,5-a]azepine derivatives was efficiently accomplished by cycloaddition of the bicyclic 1-aza-2-azoniaallene salts 6, derived from 6,7-dihydrobenzo[b]thiophen-4(5H)-one hydrazones 4, to the triple bond of nitriles, followed by ring enlargement. The X-ray crystal diffraction analysis of the picrate 10a provided affirmative proof for the structural assignment made.",

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author = "Quanrui Wang and Zheng Li and Haiyan Yang and Feng Li and Zongbiao Ding and Fenggang Tao",

year = "2003",

doi = "10.1055/s-2003-39392",

language = "English (US)",

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journal = "Synthesis",

issn = "0039-7881",

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TY - JOUR

T1 - Annulated 1,2,4-triazoles. A convenient synthesis of thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines

T2 - A novel triheterocyclic ring system

AU - Wang, Quanrui

AU - Li, Zheng

AU - Yang, Haiyan

AU - Li, Feng

AU - Ding, Zongbiao

AU - Tao, Fenggang

PY - 2003

Y1 - 2003

N2 - A synthetic approach to the previously unknown thieno[2,3-f][1,2,4]triazolo[1,5-a]azepine derivatives was efficiently accomplished by cycloaddition of the bicyclic 1-aza-2-azoniaallene salts 6, derived from 6,7-dihydrobenzo[b]thiophen-4(5H)-one hydrazones 4, to the triple bond of nitriles, followed by ring enlargement. The X-ray crystal diffraction analysis of the picrate 10a provided affirmative proof for the structural assignment made.

AB - A synthetic approach to the previously unknown thieno[2,3-f][1,2,4]triazolo[1,5-a]azepine derivatives was efficiently accomplished by cycloaddition of the bicyclic 1-aza-2-azoniaallene salts 6, derived from 6,7-dihydrobenzo[b]thiophen-4(5H)-one hydrazones 4, to the triple bond of nitriles, followed by ring enlargement. The X-ray crystal diffraction analysis of the picrate 10a provided affirmative proof for the structural assignment made.

KW - 1-aza-2-azoniaallene cations

KW - Cycloaddition

KW - Nitriles

KW - Ring enlargement

KW - Thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines

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U2 - 10.1055/s-2003-39392

DO - 10.1055/s-2003-39392

M3 - Article

AN - SCOPUS:0038726022

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JO - Synthesis

JF - Synthesis

IS - 8

ER -

Annulated 1,2,4-triazoles. A convenient synthesis of thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines: A novel triheterocyclic ring system

Abstract

Keywords

ASJC Scopus subject areas

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