Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence

Amarendar Reddy Maddirala; Peter R Andreana

doi:10.3762/bjoc.14.74

Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence

Beilstein J Org Chem. 2018 Apr 18:14:875-883. doi: 10.3762/bjoc.14.74. eCollection 2018.

Authors

Amarendar Reddy Maddirala¹, Peter R Andreana¹

Affiliation

¹ Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606, USA.

Abstract

The synthesis of spiro[indoline-3,2'-pyrrole]-2,5'(1'H)-diones and spiro[indoline-3,2'-pyrrolidine]-2,5'-diones, via a post-Ugi-domino transamidation/cyclization sequential process, has been achieved in three sequential steps utilizing a one-pot reaction protocol. The variation in carboxylic acid substrates allows for the generation of new chiral racemic quaternary carbon centers under basic conditions providing molecular diversity and a small library of spirocyclic oxindoles.

Keywords: convertible isocyanides; lactams; molecular diversity; oxindoles; transamidation.