Cycloadditions to pyrrolo[1,2-c]thiazoles and pyrazolo[1,5-c]thiazoles

O B  Sutcliffe; R C  Storr; T L  Gilchrist; P  Rafferty

doi:10.1016/S0040-4020(00)00956-X

Cycloadditions to pyrrolo[1,2-c]thiazoles and pyrazolo[1,5-c]thiazoles

O B Sutcliffe, R C Storr, T L Gilchrist, P Rafferty

Strathclyde Institute Of Pharmacy And Biomedical Sciences

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

29 Citations (Scopus)

Abstract

The pyrrolo[1,2-c]thiazole generated by dehydration of dimethyl 5-methyl-1H,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylate 2-oxide acts as a thiocarbonyl ylide in its cycloaddition to electron deficient alkenes but as an azomethine ylide with electron deficient alkynes. The analogous pyrazolo[1,5-c]thiazole, generated similarly, acts as a thiocarbonyl ylide with both types of dipolarophile. This behaviour is partially explained by Frontier MO theory.

Original language	English
Pages (from-to)	10011-10021
Number of pages	11
Journal	Tetrahedron
Volume	56
Issue number	51
Early online date	6 Dec 2000
DOIs	https://doi.org/10.1016/S0040-4020(00)00956-X
Publication status	Published - 15 Dec 2000

Keywords

dipolar cycloaddition
thiocarbonyl ylide
azomethine ylide
pyrrolo[1,2-c]thiazole
pyrazolo[1,5-c]thiazole
frontier MO theory
thiazole system
parameters

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title = "Cycloadditions to pyrrolo[1,2-c]thiazoles and pyrazolo[1,5-c]thiazoles",

abstract = "The pyrrolo[1,2-c]thiazole generated by dehydration of dimethyl 5-methyl-1H,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylate 2-oxide acts as a thiocarbonyl ylide in its cycloaddition to electron deficient alkenes but as an azomethine ylide with electron deficient alkynes. The analogous pyrazolo[1,5-c]thiazole, generated similarly, acts as a thiocarbonyl ylide with both types of dipolarophile. This behaviour is partially explained by Frontier MO theory.",

keywords = "dipolar cycloaddition, thiocarbonyl ylide, azomethine ylide, pyrrolo[1,2-c]thiazole, pyrazolo[1,5-c]thiazole, frontier MO theory, thiazole system, parameters",

author = "Sutcliffe, {O B} and Storr, {R C} and Gilchrist, {T L} and P Rafferty",

year = "2000",

month = dec,

day = "15",

doi = "10.1016/S0040-4020(00)00956-X",

language = "English",

volume = "56",

pages = "10011--10021",

journal = "Tetrahedron",

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number = "51",

}

TY - JOUR

T1 - Cycloadditions to pyrrolo[1,2-c]thiazoles and pyrazolo[1,5-c]thiazoles

AU - Sutcliffe, O B

AU - Storr, R C

AU - Gilchrist, T L

AU - Rafferty, P

PY - 2000/12/15

Y1 - 2000/12/15

N2 - The pyrrolo[1,2-c]thiazole generated by dehydration of dimethyl 5-methyl-1H,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylate 2-oxide acts as a thiocarbonyl ylide in its cycloaddition to electron deficient alkenes but as an azomethine ylide with electron deficient alkynes. The analogous pyrazolo[1,5-c]thiazole, generated similarly, acts as a thiocarbonyl ylide with both types of dipolarophile. This behaviour is partially explained by Frontier MO theory.

AB - The pyrrolo[1,2-c]thiazole generated by dehydration of dimethyl 5-methyl-1H,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylate 2-oxide acts as a thiocarbonyl ylide in its cycloaddition to electron deficient alkenes but as an azomethine ylide with electron deficient alkynes. The analogous pyrazolo[1,5-c]thiazole, generated similarly, acts as a thiocarbonyl ylide with both types of dipolarophile. This behaviour is partially explained by Frontier MO theory.

KW - dipolar cycloaddition

KW - thiocarbonyl ylide

KW - azomethine ylide

KW - pyrrolo[1,2-c]thiazole

KW - pyrazolo[1,5-c]thiazole

KW - frontier MO theory

KW - thiazole system

KW - parameters

U2 - 10.1016/S0040-4020(00)00956-X

DO - 10.1016/S0040-4020(00)00956-X

M3 - Article

SN - 0040-4020

VL - 56

SP - 10011

EP - 10021

JO - Tetrahedron

JF - Tetrahedron

IS - 51

ER -

Cycloadditions to pyrrolo[1,2-c]thiazoles and pyrazolo[1,5-c]thiazoles

Abstract

Keywords

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