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

[ Vol. 12 , Issue. 4 ]

Author(s):

Valeriya S. Velezheva, Irina N. Fedorova, Olesya L. Babii, Alexei A. Anisimov, Ivan S. Bushmarinov and Aleksander S. Peregudov   Pages 457 - 465 ( 9 )

Abstract:


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.

Affiliation:

A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, 119991 GSP-1 Moscow, Russia.

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