One-Pot Transannulation of N-Sulfonyl-1,2,3-triazoles to Dihydro-ß-carbolines and Dihydroisoquinolines via Rhodium-Catalyzed C-H Insertion-cum-Base-Mediated Aza-Michael Reaction.
J Org Chem
; 84(12): 7747-7761, 2019 06 21.
Article
em En
| MEDLINE
| ID: mdl-31132245
ABSTRACT
Efficient one-pot rhodium-catalyzed and base-mediated transannulation of N-sulfonyl-1,2,3-triazoles with a Michael acceptor-tethered indole derivative have been achieved for the synthesis of dihydro-ß-carboline derivatives. The present methodology involves an efficient rhodium-catalyzed insertion of azavinyl carbenes to C3-H bond of indole followed by base-mediated intramolecular aza-Michael reaction. The optimized conditions tolerate various functional groups and afford the diverse dihydro-ß-carbolines in good yield. The method was successfully extended to the synthesis of dihydroisoquinolines employing Michael acceptor-tethered aniline derivatives. The potential of the developed method was demonstrated through one-pot cascade synthesis of dihydro-ß-carbolines from alkyne and their conversion to vital carboline derivatives.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
Índia