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Current Organic Synthesis


ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Diastereoselective Synthesis of Dispiropseudoindoxyls and Preparation of 9-Oxopyrrolo[ 1,2-α]Indoles

Author(s): Valeriya S. Velezheva, Irina N. Fedorova, Olesya L. Babii, Alexei A. Anisimov, Ivan S. Bushmarinov and Aleksander S. Peregudov

Volume 12, Issue 4, 2015

Page: [457 - 465] Pages: 9

DOI: 10.2174/1570179412666150305232136

Price: $65


Reported here are two novel cationic domino reactions of 2-arylmethylideneindoxyls leading to the formation of highly substituted dispiropseudoindoxyls or 9-oxo-pyrrolo[1,2-α]indoles. The outcome of the reactions can be controlled by the appropriate choice of an acid or the application of an external nucleophile. The dispirocyclodimers are formed in single diastereomeric forms with three stereogenic centers, with two of those being quaternary. The reactions provide approaches to the spiropseudoindoxyl and pyrrolo[1,2-α]indole ring systems, common components in natural spiropseudoindoxyl alkaloids and pyrrolo[1,2-α]indole biologically active molecules.

Keywords: 2-Arylmethylideneindoxyls, , diastereoselective dispirocyclodimerization, dispiropseudoindoxyls, domino reactions, 9-Oxo-pyrrolo[1, 2-α]indoles.

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