Synlett 2019; 30(10): 1231-1236
DOI: 10.1055/s-0037-1611816
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Spiro-2H-pyrroles from N-Propargylic β-Enaminones

Eda Karadeniz
,
Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey   Email: zora@metu.edu.tr
› Author Affiliations
We thank the Türkiye Bilimsel ve Teknolojik Araştirma Kurumu (Scientific and Technological Research Council of Turkey, TUBITAK; Grant No. 114Z811) and the Orta Doğu Teknik Üniversitesi (Middle East Technical University, METU; Grant No. GAP-103-2018-2770) for financial support of this research.
Further Information

Publication History

Received: 28 February 2019

Accepted after revision: 12 April 2019

Publication Date:
03 May 2019 (online)


Abstract

A simple and general one-pot method for the synthesis of spiro-2H-pyrroles has been developed. Initially, cyclohexane-embedded β-enaminones with internal alkyne functionality were synthesized by conjugate addition of 1-ethynylcyclohexylamine to α,β-alkynic ketones, followed by palladium-catalyzed coupling of the resulting N-propargylic β-enaminones with aryl iodides. When subjected to basic conditions, the cyclohexane-embedded β-enaminones with internal alkyne functionality underwent tandem nucleophilic cyclization and benzylic C–H oxidation to furnish 3,4-diaryloyl-1-azaspiro[4.5]deca-1,3-diene derivatives in good yields.

Supporting Information

 
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