Steric-Hindrance-Induced Diastereoselective Radical Nitration of 3-Alkylidene-2-oxindoles Followed by Tosylhydrazine-Mediated Sulfonation.

Pramanik, Sayan; Saha, Pinaki; Ghosh, Prasanta; Mukhopadhyay, Chhanda

Pramanik, Sayan; Saha, Pinaki; Ghosh, Prasanta; Mukhopadhyay, Chhanda.

Afiliación

Pramanik S; Department of Chemistry, University of Calcutta, 92 APC Road, Kolkata 700009, India.
Saha P; Department of Chemistry, R. K. Mission Residential College, Narendrapur, Kolkata 700103, India.
Ghosh P; Department of Chemistry, R. K. Mission Residential College, Narendrapur, Kolkata 700103, India.
Mukhopadhyay C; Department of Chemistry, University of Calcutta, 92 APC Road, Kolkata 700009, India.

J Org Chem ; 88(6): 3386-3402, 2023 Mar 17.

Article en En | MEDLINE | ID: mdl-36847251

RESUMEN

Metal-free radical nitration of the ß C-H bond of 3-alkylidene-2-oxindoles with tert-butyl nitrite (TBN) has been explored. Interestingly, (E)-3-(2-(aryl)-2-oxoethylidene)oxindole and (E)-3-ylidene oxindole give different diastereomers on nitration. The mechanistic investigation revealed that the diastereoselectivity was controlled by the size of the functional group. Another transformation of 3-(nitroalkylidene) oxindole into 3-(tosylalkylidene) oxindole was performed through metal and oxidant-free tosylhydrazine-mediated sulfonation. Both methods have the advantages of readily available starting materials and operational simplicity.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2023 Tipo del documento: Article País de afiliación: India Pais de publicación: Estados Unidos

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