Azide-Triggered Bicyclization of o-Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5-a]quinolines

Onnicha Khaikate; Darunee Soorukram; Pawaret Leowanawat; Manat Pohmakotr; Vichai Reutrakul; Chutima Kuhakarn

doi:10.1002/ejoc.201901209

Azide-Triggered Bicyclization of o-Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5-a]quinolines

Onnicha Khaikate
, Darunee Soorukram
, Pawaret Leowanawat
, Manat Pohmakotr
, Vichai Reutrakul
, Chutima Kuhakarn

Mahidol University

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

14 Citations (Scopus)

Abstract

An efficient and rapid synthetic approach for the synthesis of tetrazolo[1,5-a]quinolines has been developed employing the reaction of o-alkynylisocyanobenzenes with sodium azide. The present strategy involved nucleophilic addition of azide to isocyanide followed by 6-endo cyclization. The reaction gives access to a collection of tetrazolo[1,5-a]quinolines with broad functional group in moderate to high yields under metal-, and base-free conditions.

Original language	English
Pages (from-to)	7050-7057
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	42
DOIs	https://doi.org/10.1002/ejoc.201901209
Publication status	Published - 14 Nov 2019
Externally published	Yes

Keywords

Cyclization
Isocyanides
Nitrogen heterocycles
Synthetic methods

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10.1002/ejoc.201901209

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title = "Azide-Triggered Bicyclization of o-Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5-a]quinolines",

abstract = "An efficient and rapid synthetic approach for the synthesis of tetrazolo[1,5-a]quinolines has been developed employing the reaction of o-alkynylisocyanobenzenes with sodium azide. The present strategy involved nucleophilic addition of azide to isocyanide followed by 6-endo cyclization. The reaction gives access to a collection of tetrazolo[1,5-a]quinolines with broad functional group in moderate to high yields under metal-, and base-free conditions.",

keywords = "Cyclization, Isocyanides, Nitrogen heterocycles, Synthetic methods",

author = "Onnicha Khaikate and Darunee Soorukram and Pawaret Leowanawat and Manat Pohmakotr and Vichai Reutrakul and Chutima Kuhakarn",

note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

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doi = "10.1002/ejoc.201901209",

language = "English",

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T1 - Azide-Triggered Bicyclization of o-Alkynylisocyanobenzenes

T2 - Synthesis of Tetrazolo[1,5-a]quinolines

AU - Khaikate, Onnicha

AU - Soorukram, Darunee

AU - Leowanawat, Pawaret

AU - Pohmakotr, Manat

AU - Reutrakul, Vichai

AU - Kuhakarn, Chutima

PY - 2019/11/14

Y1 - 2019/11/14

N2 - An efficient and rapid synthetic approach for the synthesis of tetrazolo[1,5-a]quinolines has been developed employing the reaction of o-alkynylisocyanobenzenes with sodium azide. The present strategy involved nucleophilic addition of azide to isocyanide followed by 6-endo cyclization. The reaction gives access to a collection of tetrazolo[1,5-a]quinolines with broad functional group in moderate to high yields under metal-, and base-free conditions.

AB - An efficient and rapid synthetic approach for the synthesis of tetrazolo[1,5-a]quinolines has been developed employing the reaction of o-alkynylisocyanobenzenes with sodium azide. The present strategy involved nucleophilic addition of azide to isocyanide followed by 6-endo cyclization. The reaction gives access to a collection of tetrazolo[1,5-a]quinolines with broad functional group in moderate to high yields under metal-, and base-free conditions.

KW - Cyclization

KW - Isocyanides

KW - Nitrogen heterocycles

KW - Synthetic methods

UR - https://www.scopus.com/pages/publications/85074416371

U2 - 10.1002/ejoc.201901209

DO - 10.1002/ejoc.201901209

M3 - Article

AN - SCOPUS:85074416371

SN - 1434-193X

VL - 2019

SP - 7050

EP - 7057

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 42

ER -

Azide-Triggered Bicyclization of o-Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5-a]quinolines

Abstract

Keywords

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