Events The 17th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 17th International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 2013

Citation

Vasiliy Yu. Stolyarenko, Ananatoliy A. Evdokimov, Vladimir I. Shishkin, Synthesis of spiro-annelated γ-lactams by isocyanide-based multicomponent reactions involving hem-disubstituted bifunctional reagents, in Proceedings of The 17th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2013, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-17-a047

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Synthesis of spiro-annelated γ-lactams by isocyanide-based multicomponent reactions involving hem-disubstituted bifunctional reagents

Vasiliy Yu. Stolyarenko ¹

Ananatoliy A. Evdokimov ¹

Vladimir I. Shishkin ¹

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

Manuscript

SVY_EcsOS.pdf

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