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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)164-167
Number of pages4
JournalOrganic Letters
Volume12
Issue number1
DOIs
StatePublished - Jan 1 2010

Fingerprint

Triazines
Pyrroles
pyrroles
Hydrazones
hydrazones
Oximes
Cycloaddition
rings
Cycloaddition Reaction
cycloaddition
adducts
1,2,4-triazine
pyrrolidine

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Ye, L., Haddadin, M. J., Lodewyk, M. W., Ferreira, A. J., Fettinger, J. C., Tantillo, D. J., & Kurth, M. J. (2010). Cyclopenta[b]pyrroles from triazines: synthetic and mechanistic studies. Organic Letters, 12(1), 164-167. https://doi.org/10.1021/ol902559u

Cyclopenta[b]pyrroles from triazines : synthetic and mechanistic studies. / Ye, Long; Haddadin, Makhluf J.; Lodewyk, Michael W.; Ferreira, Andrew J.; Fettinger, James C.; Tantillo, Dean J.; Kurth, Mark J.

In: Organic Letters, Vol. 12, No. 1, 01.01.2010, p. 164-167.

Research output: Contribution to journalArticle

Ye, L, Haddadin, MJ, Lodewyk, MW, Ferreira, AJ, Fettinger, JC, Tantillo, DJ & Kurth, MJ 2010, 'Cyclopenta[b]pyrroles from triazines: synthetic and mechanistic studies', Organic Letters, vol. 12, no. 1, pp. 164-167. https://doi.org/10.1021/ol902559u
Ye L, Haddadin MJ, Lodewyk MW, Ferreira AJ, Fettinger JC, Tantillo DJ et al. Cyclopenta[b]pyrroles from triazines: synthetic and mechanistic studies. Organic Letters. 2010 Jan 1;12(1):164-167. https://doi.org/10.1021/ol902559u
Ye, Long ; Haddadin, Makhluf J. ; Lodewyk, Michael W. ; Ferreira, Andrew J. ; Fettinger, James C. ; Tantillo, Dean J. ; Kurth, Mark J. / Cyclopenta[b]pyrroles from triazines : synthetic and mechanistic studies. In: Organic Letters. 2010 ; Vol. 12, No. 1. pp. 164-167.
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