Piperazine as leaving group in A3 adducts: Fast access to alkynyl indoles

Mansour Dolè Kerim; Laurent El Kaïm

doi:10.1055/s-0035-1561396

Piperazine as leaving group in A3 adducts: Fast access to alkynyl indoles

Mansour Dolè Kerim
, Laurent El Kaïm

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

5 Citations (Scopus)

Abstract

The A3 coupling between N-ethylpiperazine and electron-rich aromatic aldehydes forms adducts that may be easily used as electrophiles towards electron-rich heterocycles such as indoles. The removal of the piperazine moiety is triggered by the addition of 1,2-dibromoethane. Overall, the reaction provides efficient access to alkynyl indoles and pyrroles.

Original language	English
Article number	st-2016-d0042-l
Pages (from-to)	1572-1576
Number of pages	5
Journal	Synlett
Volume	27
Issue number	10
DOIs	https://doi.org/10.1055/s-0035-1561396
Publication status	Published - 2 Jun 2016

Keywords

A3 reaction
alkyne
indoles
piperazine

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10.1055/s-0035-1561396

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title = "Piperazine as leaving group in A3 adducts: Fast access to alkynyl indoles",

abstract = "The A3 coupling between N-ethylpiperazine and electron-rich aromatic aldehydes forms adducts that may be easily used as electrophiles towards electron-rich heterocycles such as indoles. The removal of the piperazine moiety is triggered by the addition of 1,2-dibromoethane. Overall, the reaction provides efficient access to alkynyl indoles and pyrroles.",

keywords = "A3 reaction, alkyne, indoles, piperazine",

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AU - Kerim, Mansour Dolè

AU - El Kaïm, Laurent

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

PY - 2016/6/2

Y1 - 2016/6/2

N2 - The A3 coupling between N-ethylpiperazine and electron-rich aromatic aldehydes forms adducts that may be easily used as electrophiles towards electron-rich heterocycles such as indoles. The removal of the piperazine moiety is triggered by the addition of 1,2-dibromoethane. Overall, the reaction provides efficient access to alkynyl indoles and pyrroles.

AB - The A3 coupling between N-ethylpiperazine and electron-rich aromatic aldehydes forms adducts that may be easily used as electrophiles towards electron-rich heterocycles such as indoles. The removal of the piperazine moiety is triggered by the addition of 1,2-dibromoethane. Overall, the reaction provides efficient access to alkynyl indoles and pyrroles.

KW - A3 reaction

KW - alkyne

KW - indoles

KW - piperazine

U2 - 10.1055/s-0035-1561396

DO - 10.1055/s-0035-1561396

M3 - Article

AN - SCOPUS:84962050735

SN - 0936-5214

VL - 27

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JF - Synlett

IS - 10

M1 - st-2016-d0042-l

ER -

Piperazine as leaving group in A3 adducts: Fast access to alkynyl indoles

Abstract

Keywords

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