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

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.

SUBMITTER: Maddirala AR

PROVIDER: S-EPMC5942382 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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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.

Maddirala Amarendar Reddy AR Andreana Peter R PR

Beilstein journal of organic chemistry 20180418

The synthesis of spiro[indoline-3,2'-pyrrole]-2,5'(1'<i>H</i>)-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. ...[more]

PMID: 29765468

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