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Synlett 2021; 32(06): 621-625
DOI: 10.1055/a-1308-3773
letter

Synthesis of Spiro Oxazolidinedione Analogues Based on Tandem Multicyclizations of 1,3-Dimethylalloxan and Enaminones in Water

Tina Abbasi
a   Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
,
Mohammad Bagher Teimouri  ∗
b   Department of Chemistry, Kharazmi University, Tehran, Iran
,
Issa Yavari  ∗
c   Department of Chemistry, Tarbiat Modares University, Tehran, Iran
,
Rahman Bikas
d   Department of Chemistry, Imam Khomeini International University, Qazvin, Iran
› Author AffiliationsThe financial support of Kharazmi University (grant number D/2047) is gratefully acknowledged.
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Abstract

A tandem double-annulation reaction of 1,3-dimethylalloxan with enaminones, generated in situ from alkyl amines and alkyl but-2-ynoates or pent-3-yn-2-ones to give functionalized oxazolidinedione spiro analogues is described. Three of the four carbonyl groups of alloxan have been engaged through a tandem Michael addition, aldol-type condensation, and double intramolecular annulation sequence.

Key words

alloxan - enaminones - multicomponent reaction - oxazolidinediones - spiroheterocycles - tandem reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1308-3773.
  • Supporting Information


Publication History

Received: 27 September 2020

Accepted after revision: 11 November 2020

Accepted Manuscript online:
11 November 2020

Article published online:
08 December 2020

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