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Synthesis of Spiro-Annelated γ-Lactams by Isocyanide-Based Multicomponent Reactions Involving Hem-Disubstituted Bifunctional Reagents
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1  Moscow State Technical University of Radioengineering Electronics and Automation

Abstract: The new bifunctional hem-disubstituted alicyclic compounds IIIa-e and IVa-e were synthesized in several steps involving alkylation with allyl bromide following oxidative cleavage. Hem-disubstitues oxo-esters IIIa-e were introduced into azido-Ugi reaction followed by one-pot intramolucular bond formation to afford 3-(tetrazol-5-yl)-2-azaspiro[4.n]alkan-1-ones. The three component Ugi reaction with isocyanides, primary amines and 1-(2-oxoethyl)cycloalkanecarboxylic acids IVa-e affords spirocyclic N-substituted pyroglutamides.
Keywords: isocyanide-based multicomponent reactions, spirocyclic compounds, γ-lactams