The preparation of 4-substituted pyrylium salts and their use in dienal synthesis

P  Charoenying; K  Hemming; D  McKerrecher; R J K  Taylor

The preparation of 4-substituted pyrylium salts and their use in dienal synthesis

P Charoenying, K Hemming, D McKerrecher, R J K Taylor

Chemistry

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

Abstract

The unsubstituted pyrylium nucleus is shown to undergo reaction with cuprate or secondary Grignard organometallic reagents to give intermediate 4-substituted pyrans which are converted into the corresponding 4-substituted pyrylium salts (7 examples) in fair to good overall yield. The synthetic utility of the 4-substituted pyrylium heterocycles is demonstrated by their reaction with organolithium reagents to give 3,5-disubstituted dienals in a highly stereospecific manner (7 examples) via electrocyclic ring opening of the intermediate 2-substituted pyrans.

Original language	English
Pages (from-to)	1083-1089
Number of pages	7
Journal	JOURNAL OF HETEROCYCLIC CHEMISTRY
Volume	33
Issue number	4
Publication status	Published - 1996

Keywords

CONVENIENT METHOD
STEREOSELECTIVE SYNTHESIS
REGIOSELECTIVE SYNTHESIS
REAGENTS
4-ALKYL(ARYL)PYRIDINES

Cite this

@article{518b5148c1d04f1eb96d042325473963,

title = "The preparation of 4-substituted pyrylium salts and their use in dienal synthesis",

abstract = "The unsubstituted pyrylium nucleus is shown to undergo reaction with cuprate or secondary Grignard organometallic reagents to give intermediate 4-substituted pyrans which are converted into the corresponding 4-substituted pyrylium salts (7 examples) in fair to good overall yield. The synthetic utility of the 4-substituted pyrylium heterocycles is demonstrated by their reaction with organolithium reagents to give 3,5-disubstituted dienals in a highly stereospecific manner (7 examples) via electrocyclic ring opening of the intermediate 2-substituted pyrans.",

keywords = "CONVENIENT METHOD, STEREOSELECTIVE SYNTHESIS, REGIOSELECTIVE SYNTHESIS, REAGENTS, 4-ALKYL(ARYL)PYRIDINES",

author = "P Charoenying and K Hemming and D McKerrecher and Taylor, {R J K}",

year = "1996",

language = "English",

volume = "33",

pages = "1083--1089",

journal = "JOURNAL OF HETEROCYCLIC CHEMISTRY",

issn = "0022-152X",

publisher = "John Wiley and Sons Inc.",

number = "4",

}

TY - JOUR

T1 - The preparation of 4-substituted pyrylium salts and their use in dienal synthesis

AU - Charoenying, P

AU - Hemming, K

AU - McKerrecher, D

AU - Taylor, R J K

PY - 1996

Y1 - 1996

N2 - The unsubstituted pyrylium nucleus is shown to undergo reaction with cuprate or secondary Grignard organometallic reagents to give intermediate 4-substituted pyrans which are converted into the corresponding 4-substituted pyrylium salts (7 examples) in fair to good overall yield. The synthetic utility of the 4-substituted pyrylium heterocycles is demonstrated by their reaction with organolithium reagents to give 3,5-disubstituted dienals in a highly stereospecific manner (7 examples) via electrocyclic ring opening of the intermediate 2-substituted pyrans.

AB - The unsubstituted pyrylium nucleus is shown to undergo reaction with cuprate or secondary Grignard organometallic reagents to give intermediate 4-substituted pyrans which are converted into the corresponding 4-substituted pyrylium salts (7 examples) in fair to good overall yield. The synthetic utility of the 4-substituted pyrylium heterocycles is demonstrated by their reaction with organolithium reagents to give 3,5-disubstituted dienals in a highly stereospecific manner (7 examples) via electrocyclic ring opening of the intermediate 2-substituted pyrans.

KW - CONVENIENT METHOD

KW - STEREOSELECTIVE SYNTHESIS

KW - REGIOSELECTIVE SYNTHESIS

KW - REAGENTS

KW - 4-ALKYL(ARYL)PYRIDINES

M3 - Article

SN - 0022-152X

VL - 33

SP - 1083

EP - 1089

JO - JOURNAL OF HETEROCYCLIC CHEMISTRY

JF - JOURNAL OF HETEROCYCLIC CHEMISTRY

IS - 4

ER -