Synthesis of Indolizines via Reaction of 2-Substitued Azaarenes with Enals by an Amine-NHC Relay Catalysis

Hongxian Li; Xiangmin Li; Yang Yu; Jianjun Li; Yuan Liu; Hao Li; Wei Wang

doi:10.1021/acs.orglett.7b00566

Synthesis of Indolizines via Reaction of 2-Substitued Azaarenes with Enals by an Amine-NHC Relay Catalysis

Hongxian Li, Xiangmin Li, Yang Yu, Jianjun Li, Yuan Liu, Hao Li, Wei Wang

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

47 Scopus citations

Abstract

A metal-free catalytic strategy for the facile synthesis of biologically relevant molecular architectures indolizines and imidazopyridines has been developed. The process is promoted by amine and N-heterocyclic carbene (NHC) relay catalysis via Michael addition-[3 + 2] fusion of simple azaarenes and α,β-unsaturated aldehydes. The preparative power is demonstrated in the synthesis of anxiolytic drug saripidem via two simple one-pot operations with overall 45% yield.

Original language	English (US)
Pages (from-to)	2010-2013
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.7b00566
State	Published - Apr 21 2017
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b00566

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title = "Synthesis of Indolizines via Reaction of 2-Substitued Azaarenes with Enals by an Amine-NHC Relay Catalysis",

abstract = "A metal-free catalytic strategy for the facile synthesis of biologically relevant molecular architectures indolizines and imidazopyridines has been developed. The process is promoted by amine and N-heterocyclic carbene (NHC) relay catalysis via Michael addition-[3 + 2] fusion of simple azaarenes and α,β-unsaturated aldehydes. The preparative power is demonstrated in the synthesis of anxiolytic drug saripidem via two simple one-pot operations with overall 45% yield.",

author = "Hongxian Li and Xiangmin Li and Yang Yu and Jianjun Li and Yuan Liu and Hao Li and Wei Wang",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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T1 - Synthesis of Indolizines via Reaction of 2-Substitued Azaarenes with Enals by an Amine-NHC Relay Catalysis

AU - Li, Hongxian

AU - Li, Xiangmin

AU - Yu, Yang

AU - Li, Jianjun

AU - Liu, Yuan

AU - Li, Hao

AU - Wang, Wei

PY - 2017/4/21

Y1 - 2017/4/21

N2 - A metal-free catalytic strategy for the facile synthesis of biologically relevant molecular architectures indolizines and imidazopyridines has been developed. The process is promoted by amine and N-heterocyclic carbene (NHC) relay catalysis via Michael addition-[3 + 2] fusion of simple azaarenes and α,β-unsaturated aldehydes. The preparative power is demonstrated in the synthesis of anxiolytic drug saripidem via two simple one-pot operations with overall 45% yield.

AB - A metal-free catalytic strategy for the facile synthesis of biologically relevant molecular architectures indolizines and imidazopyridines has been developed. The process is promoted by amine and N-heterocyclic carbene (NHC) relay catalysis via Michael addition-[3 + 2] fusion of simple azaarenes and α,β-unsaturated aldehydes. The preparative power is demonstrated in the synthesis of anxiolytic drug saripidem via two simple one-pot operations with overall 45% yield.

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JO - Organic Letters

JF - Organic Letters

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ER -

Synthesis of Indolizines via Reaction of 2-Substitued Azaarenes with Enals by an Amine-NHC Relay Catalysis

Abstract

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