Regioselective copper-mediated synthesis of thieno[2,3-c]pyrane-7-one, indolo[2,3-c]pyrane-1-one, and indolo[3,2-c]pyrane-1-one

Samuel Inack Ngi; Vincent Guilloteau; Mohamed Abarbri; Jérôme Thibonnet

doi:10.1021/jo201528u

Regioselective copper-mediated synthesis of thieno[2,3-c]pyrane-7-one, indolo[2,3-c]pyrane-1-one, and indolo[3,2-c]pyrane-1-one

J Org Chem. 2011 Oct 21;76(20):8347-54. doi: 10.1021/jo201528u. Epub 2011 Sep 15.

Authors

Samuel Inack Ngi¹, Vincent Guilloteau, Mohamed Abarbri, Jérôme Thibonnet

Affiliation

¹ Laboratoire de Physicochimie des Matériaux et des Biomolécules, EA 4244, Faculté des Sciences et Techniques de Tours, Parc de Grandmont, 37200 Tours, France.

PMID: 21882812
DOI: 10.1021/jo201528u

Abstract

In the presence of copper(I) iodide, heteroaromatic β-iodo-α,β-unsaturated carboxylic acid systems opposed to terminal alkyne afford selectively 6-endo-dig cyclization products via a tandem coupling oxacyclization reaction.

MeSH terms

Alkynes / chemistry
Carboxylic Acids / chemistry
Catalysis
Chemistry, Pharmaceutical / methods*
Copper / chemistry
Cyclization
Indoles / chemical synthesis*
Iodides / chemistry
Magnetic Resonance Spectroscopy
Pyrans / chemical synthesis*
Stereoisomerism
Thiophenes / chemical synthesis*

Substances

Alkynes
Carboxylic Acids
Indoles
Iodides
Pyrans
Thiophenes
Copper