Transition-Metal-Free, Atom- and Step-Economic Synthesis of Aminoketopyrrolizines from Benzylamine, Acylethynylpyrroles, and Acylacetylenes

Lyubov' N Sobenina; Denis N Tomilin; Elena F Sagitova; Igor' A Ushakov; Boris A Trofimov

doi:10.1021/acs.orglett.7b00408

Transition-Metal-Free, Atom- and Step-Economic Synthesis of Aminoketopyrrolizines from Benzylamine, Acylethynylpyrroles, and Acylacetylenes

Org Lett. 2017 Apr 7;19(7):1586-1589. doi: 10.1021/acs.orglett.7b00408. Epub 2017 Mar 21.

Authors

Lyubov' N Sobenina¹, Denis N Tomilin¹, Elena F Sagitova¹, Igor' A Ushakov¹, Boris A Trofimov¹

Affiliation

¹ A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences , 1 Favorsky Str, 664033 Irkutsk, Russian Federation.

PMID: 28322568
DOI: 10.1021/acs.orglett.7b00408

Abstract

A concise, atom-economic strategy for the synthesis of pyrrolizines with amino and keto substituents has been developed. It includes the following key steps: (i) the base-catalyzed (K₃PO₄/DMSO) addition of a benzylamine to 2-acylethynylpyrroles and (ii) noncatalyzed addition of enaminones obtained to the triple bond of acylacetylenes followed by intramolecular cyclization of the intermediate pentadiendiones thus formed to the target 1-(benzylamino)-2-acyl-3-methylenoacylpyrrolizines.

Publication types

Research Support, Non-U.S. Gov't