Synlett 2021; 32(20): 2080-2084
DOI: 10.1055/s-0040-1720889
letter

1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides

Anand Vala 
a   Piramal Discovery Solutions, Pharmaceutical Special Economic Zone, Sarkhej, Bavla Highway, Ahmedabad, Gujarat 382213, India
b   Department of Chemistry, Faculty of Science, The Madhav University, Pindwara (Sirohi)-307026, Rajasthan, India
,
Nirali Parmar
a   Piramal Discovery Solutions, Pharmaceutical Special Economic Zone, Sarkhej, Bavla Highway, Ahmedabad, Gujarat 382213, India
,
Jigar Y Soni
b   Department of Chemistry, Faculty of Science, The Madhav University, Pindwara (Sirohi)-307026, Rajasthan, India
,
Sharadsrikar Kotturi
a   Piramal Discovery Solutions, Pharmaceutical Special Economic Zone, Sarkhej, Bavla Highway, Ahmedabad, Gujarat 382213, India
,
Ramakrishna Guduru∗
a   Piramal Discovery Solutions, Pharmaceutical Special Economic Zone, Sarkhej, Bavla Highway, Ahmedabad, Gujarat 382213, India
› Author AffiliationsPiramal Pharma Solutions, India.
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1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto AmidesSynlett 2021; 32(20): e2-e2
DOI: 10.1055/s-0040-1720920

Abstract

Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen’s rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.

Key words

dioxazolones - isocyanates - keto amides - quinolinones - Lossen rearrangement

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720889.
  • Supporting Information


Publication History

Received: 08 June 2021

Accepted after revision: 08 September 2021

Article published online:
28 September 2021

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