Aza-annulation of enaminones with crotonyl chloride - Formal reversal of regioselectivity.

JP Murphy; M Hadden; PJ Stevenson

Aza-annulation of enaminones with crotonyl chloride - Formal reversal of regioselectivity.

JP Murphy
, M Hadden
, PJ Stevenson

School of Chemistry and Chemical Engineering

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

15 Citations (Scopus)

Abstract

The regiochemistry of aza-annulation of enaminones with alpha,beta-unsaturated acid chlorides bearing hydrogen atoms on the gamma-carbon is reversed when triethylamine is used as mediator. When the reaction was carried out at lower temperatures as 3-acyl beta,gamma-unsaturated compound could be isolated which cyclised to the desired product under thermal or basic conditions. The nature of this intermediate strongly suggests that a vinyl ketene is the active acylating agent. (C) 1997 Elsevier Science Ltd.

Original language	English
Pages (from-to)	11827-11834
Number of pages	8
Journal	Tetrahedron
Volume	53
Issue number	34
Publication status	Published - 25 Aug 1997

Keywords

ALKALOIDS

Cite this

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title = "Aza-annulation of enaminones with crotonyl chloride - Formal reversal of regioselectivity.",

abstract = "The regiochemistry of aza-annulation of enaminones with alpha,beta-unsaturated acid chlorides bearing hydrogen atoms on the gamma-carbon is reversed when triethylamine is used as mediator. When the reaction was carried out at lower temperatures as 3-acyl beta,gamma-unsaturated compound could be isolated which cyclised to the desired product under thermal or basic conditions. The nature of this intermediate strongly suggests that a vinyl ketene is the active acylating agent. (C) 1997 Elsevier Science Ltd.",

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T1 - Aza-annulation of enaminones with crotonyl chloride - Formal reversal of regioselectivity.

AU - Murphy, JP

AU - Hadden, M

AU - Stevenson, PJ

PY - 1997/8/25

Y1 - 1997/8/25

N2 - The regiochemistry of aza-annulation of enaminones with alpha,beta-unsaturated acid chlorides bearing hydrogen atoms on the gamma-carbon is reversed when triethylamine is used as mediator. When the reaction was carried out at lower temperatures as 3-acyl beta,gamma-unsaturated compound could be isolated which cyclised to the desired product under thermal or basic conditions. The nature of this intermediate strongly suggests that a vinyl ketene is the active acylating agent. (C) 1997 Elsevier Science Ltd.

AB - The regiochemistry of aza-annulation of enaminones with alpha,beta-unsaturated acid chlorides bearing hydrogen atoms on the gamma-carbon is reversed when triethylamine is used as mediator. When the reaction was carried out at lower temperatures as 3-acyl beta,gamma-unsaturated compound could be isolated which cyclised to the desired product under thermal or basic conditions. The nature of this intermediate strongly suggests that a vinyl ketene is the active acylating agent. (C) 1997 Elsevier Science Ltd.

KW - ALKALOIDS

M3 - Article

SN - 0040-4020

VL - 53

SP - 11827

EP - 11834

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

Aza-annulation of enaminones with crotonyl chloride - Formal reversal of regioselectivity.

Abstract

Keywords

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