Azirine-2-carbonyl Azides as C3-Synthons in the Reaction with Amidines toward 5-Aminopyrimidin-4(3 H )-ones

Daniil D. Lyakhov; Timur O. Zanakhov; Екатерина Е. Галенко; Mikhail Sergeevich Novikov; Alexander F. Khlebnikov

doi:10.1021/acs.orglett.6c02418

Azirine-2-carbonyl Azides as C3-Synthons in the Reaction with Amidines toward 5-Aminopyrimidin-4(3 H )-ones

Organic Letters 2026

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Authors: Daniil D. Lyakhov, Timur O. Zanakhov, Екатерина Е. Галенко, Mikhail Sergeevich Novikov, Alexander F. Khlebnikov

DOI: 10.1021/acs.orglett.6c02418

Cited by: 1

References: 53

Abstract

The azide group in azirine-2-carbonyl azides provides a unique electrophilic balance of the reaction sites, allowing these compounds to be used as all-carbon C3 synthons in the synthesis of N ′, N ′-unsubstituted 5-aminopyrimidin-4-ones via a (3 + 3) cyclocondensation reaction with amidines. Strongly basic conditions alter the reactivity of the key intermediate 2,4,7-triazabicyclo[4.1.0]hept-2-en-5-one, resulting in a formal (4 + 3) cyclocondensation reaction to afford 3,7-dihydro-6 H -1,3,5-triazepin-6-ones as the sole products.

Fields of Study & Subjects

Synthesis and Catalytic Reactions Chemical Reactions and Mechanisms Synthesis and Reactivity of Sulfur-Containing Compounds

Publication details

Journal / source: Organic Letters
Publisher: American Chemical Society (ACS)
Volume: 28
Issue: 27
Pages: 8730–8735
Publication date: 29 June 2026
Language: EN

References 53