A novel and convenient method for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones; synthesis and mechanistic study

F. Faigl, Szilvia Deák, Zoltán Mucsi, Tamás Hergert, László Balázs, Boros Sándor, B. Balázs, Tamás Holczbauer, Miklós Nyerges, Béla Mátravölgyi

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

An efficient, regioselective synthesis has been developed for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones from readily available 1H-pyrroles by sequential dibromination and selective organometallic bromine/lithium exchange followed by reaction with benzophenone. Comparison of various N-substituents was shown to demonstrate the high tolerance of the transformation to functional groups. The structures of the new products were determined by spectroscopic methods and confirmed by single-crystal X-ray diffraction measurement. In addition, theoretical study of the reaction mechanism and selective functionalization of the endocyclic double bond were also presented.

Original languageEnglish
Pages (from-to)5444-5455
Number of pages12
JournalTetrahedron
Volume72
Issue number35
DOIs
Publication statusPublished - 2016

Fingerprint

Bromine
Pyrroles
Organometallics
Lithium
X-Ray Diffraction
Functional groups
Theoretical Models
Single crystals
X ray diffraction
benzophenone

Keywords

  • 5-Ylidenepyrrol-2(5H)-one
  • Bromopyrrole
  • Butyllithium
  • Mechanistic study
  • X-ray crystallography

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A novel and convenient method for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones; synthesis and mechanistic study. / Faigl, F.; Deák, Szilvia; Mucsi, Zoltán; Hergert, Tamás; Balázs, László; Sándor, Boros; Balázs, B.; Holczbauer, Tamás; Nyerges, Miklós; Mátravölgyi, Béla.

In: Tetrahedron, Vol. 72, No. 35, 2016, p. 5444-5455.

Research output: Contribution to journalArticle

Faigl, F, Deák, S, Mucsi, Z, Hergert, T, Balázs, L, Sándor, B, Balázs, B, Holczbauer, T, Nyerges, M & Mátravölgyi, B 2016, 'A novel and convenient method for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones; synthesis and mechanistic study', Tetrahedron, vol. 72, no. 35, pp. 5444-5455. https://doi.org/10.1016/j.tet.2016.07.032
Faigl, F. ; Deák, Szilvia ; Mucsi, Zoltán ; Hergert, Tamás ; Balázs, László ; Sándor, Boros ; Balázs, B. ; Holczbauer, Tamás ; Nyerges, Miklós ; Mátravölgyi, Béla. / A novel and convenient method for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones; synthesis and mechanistic study. In: Tetrahedron. 2016 ; Vol. 72, No. 35. pp. 5444-5455.
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