Cyclopenta[b]pyrroles from triazines: synthetic and mechanistic studies

Long Ye; Makhluf J. Haddadin; Michael W. Lodewyk; Andrew J. Ferreira; James C. Fettinger; Dean J. Tantillo; Mark J. Kurth

doi:10.1021/ol902559u

Cyclopenta[b]pyrroles from triazines: synthetic and mechanistic studies

Long Ye, Makhluf J. Haddadin, Michael W. Lodewyk, Andrew J. Ferreira, James C. Fettinger, Dean J. Tantillo, Mark J. Kurth

Chemistry

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8 Scopus citations

Abstract

"Chemical Equation Presented" The pyrrolidine-mediated reactions of 3,5-disubstituted 1,2,4-triazines with cyclobutanone lead to cyclopenta[b]pyrroles, which can be derivatized into hydrazones and oximes. The cyclopenta[b]pyrrole ring system likely arises through a tandem [4 + 2] cycloaddition/cycloreversion/ring rearrangement reaction. In contrast, 3,6-disubstituted 1,2,4-triazines undergo a simple nucleophilic 1,4-addition with cyclobutanone to give 1:1 adducts.

Original language	English (US)
Pages (from-to)	164-167
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	1
DOIs	https://doi.org/10.1021/ol902559u
State	Published - Jan 1 2010

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

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title = "Cyclopenta[b]pyrroles from triazines: synthetic and mechanistic studies",

abstract = "{"}Chemical Equation Presented{"} The pyrrolidine-mediated reactions of 3,5-disubstituted 1,2,4-triazines with cyclobutanone lead to cyclopenta[b]pyrroles, which can be derivatized into hydrazones and oximes. The cyclopenta[b]pyrrole ring system likely arises through a tandem [4 + 2] cycloaddition/cycloreversion/ring rearrangement reaction. In contrast, 3,6-disubstituted 1,2,4-triazines undergo a simple nucleophilic 1,4-addition with cyclobutanone to give 1:1 adducts.",

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year = "2010",

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AU - Ye, Long

AU - Haddadin, Makhluf J.

AU - Lodewyk, Michael W.

AU - Ferreira, Andrew J.

AU - Fettinger, James C.

AU - Tantillo, Dean J.

AU - Kurth, Mark J.

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AB - "Chemical Equation Presented" The pyrrolidine-mediated reactions of 3,5-disubstituted 1,2,4-triazines with cyclobutanone lead to cyclopenta[b]pyrroles, which can be derivatized into hydrazones and oximes. The cyclopenta[b]pyrrole ring system likely arises through a tandem [4 + 2] cycloaddition/cycloreversion/ring rearrangement reaction. In contrast, 3,6-disubstituted 1,2,4-triazines undergo a simple nucleophilic 1,4-addition with cyclobutanone to give 1:1 adducts.

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Cyclopenta[b]pyrroles from triazines: synthetic and mechanistic studies

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