Download PDF
Synthesis 2018; 50(24): 4883-4888
DOI: 10.1055/s-0037-1610238
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Spiro Barbiturates and Meldrum’s Acid Derivatives via a [2+2+2] Cyclotrimerization

Sambasivarao Kotha*
Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai-400076, India   Email: srk@chem.iitb.ac.in
,
Gaddamedi Sreevani
Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai-400076, India   Email: srk@chem.iitb.ac.in
› Author AffiliationsS.K. thanks Department of Science and Technology for the award of a J. C. Bose fellowship and Praj Industries for the award of chair professor (Green Chemistry). G.S. thanks the CSIR-New Delhi for the award of research fellowship. We also thank DST, New Delhi for the financial support.
Further Information

Publication History

Received: 30 May 2018

Accepted after revision: 19 July 2018

Publication Date:
14 August 2018 (online)

    Permissions and Reprints All articles of this category


Abstract

Intermolecular [2+2+2] cycloaddition of propargyl halides with 1,6-diynes was accomplished with a catalytic amount of Mo(CO)6 to generate benzyl halo barbiturates and Meldrum’s acid derivatives containing a spiro linkage. Furthermore, we have extended this methodology to synthesize linearly fused Meldrum’s acid derivatives via Diels–Alder reaction using rongalite chemistry.

Key words

barbituric acid - Meldrum’s acid - [2+2+2] cycloaddition - Mo(CO)6 - spirocycles - benzyl halides - Diels–Alder

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610238.
  • Supporting Information