Facile synthesis of 2h-benzo[h]chromenes via an arylamine-catalyzed mannich cyclization cascade reaction

Yueteng Zhang; Peng Ji; Xiang Meng; Feng Gao; Fanxun Zeng; Wei Wang

doi:10.3390/molecules26123617

Facile synthesis of 2h-benzo[h]chromenes via an arylamine-catalyzed mannich cyclization cascade reaction

Yueteng Zhang
, Peng Ji
, Xiang Meng
, Feng Gao
, Fanxun Zeng
, Wei Wang

Pharmacology and Toxicology

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

5 Scopus citations

Abstract

A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes. The notable feature of the process included the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1-and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.

Original language	English (US)
Article number	3617
Journal	Molecules
Volume	26
Issue number	12
DOIs	https://doi.org/10.3390/molecules26123617
State	Published - Jun 2 2021

Keywords

Aminocatalysis
Cascade reaction
Chromenes
Organocatalysis
Quinone methide

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules26123617

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title = "Facile synthesis of 2h-benzo[h]chromenes via an arylamine-catalyzed mannich cyclization cascade reaction",

abstract = "A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes. The notable feature of the process included the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1-and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.",

keywords = "Aminocatalysis, Cascade reaction, Chromenes, Organocatalysis, Quinone methide",

author = "Yueteng Zhang and Peng Ji and Xiang Meng and Feng Gao and Fanxun Zeng and Wei Wang",

note = "Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2021",

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doi = "10.3390/molecules26123617",

language = "English (US)",

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journal = "Molecules",

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T1 - Facile synthesis of 2h-benzo[h]chromenes via an arylamine-catalyzed mannich cyclization cascade reaction

AU - Zhang, Yueteng

AU - Ji, Peng

AU - Meng, Xiang

AU - Gao, Feng

AU - Zeng, Fanxun

AU - Wang, Wei

PY - 2021/6/2

Y1 - 2021/6/2

N2 - A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes. The notable feature of the process included the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1-and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.

AB - A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes. The notable feature of the process included the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1-and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.

KW - Aminocatalysis

KW - Cascade reaction

KW - Chromenes

KW - Organocatalysis

KW - Quinone methide

UR - https://www.scopus.com/pages/publications/85108661725

UR - https://www.scopus.com/pages/publications/85108661725#tab=citedBy

U2 - 10.3390/molecules26123617

DO - 10.3390/molecules26123617

M3 - Article

C2 - 34204782

AN - SCOPUS:85108661725

SN - 1420-3049

VL - 26

JO - Molecules

JF - Molecules

IS - 12

M1 - 3617

ER -

Facile synthesis of 2h-benzo[h]chromenes via an arylamine-catalyzed mannich cyclization cascade reaction

Abstract

Keywords

ASJC Scopus subject areas

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