This article is cited in 3 papers

Communications

Spirocyclic azetidines for drug discovery: Novel Boc-protected 7'H-spiro[azetidine-3,5'-furo[3,4-d ]pyrimidines]

A. Lukin^a, L. Vinogradova^a, K. Komarova^a, M. Krasavin<sup>bc

a</sup> M.V. Lomonosov Institute of Fine Chemical Technologies, MIREA - Russian Technological University, Moscow, Russian Federation
^b Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation
^c Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation

Abstract: A novel spirocyclic scaffold of 7'H-spiro[azetidine-3,5'-furo[3,4-d]pyrimidine] chemotype was synthesized in N-Boc-protected form. However, the scaffold was revealed to be unstable to storage when deprotected. The solution was found in the brief removal of the Boc protecting group and rapid acylation of the liberated NH-azetidine with a carboxylic acid imidazolide.

Keywords: azetidines, spirocycles, pyrimidines, instability in deprotected form, privileged scaffold, 5-nitrofuroyl.

Language: English

DOI: 10.1016/j.mencom.2023.04.008

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