Regioselectivity in electrophilic substitution of 5-aminoindoles and 5-aminoindolines: synthesis of pyrrolo [3, 2-e] indoles and isomeric pyrrolo [2, 3-f] indoles
…, A Burchat, G Weeratunga, I Watts, GI Dmitrienko
Index: Prasad; Burchat; Weeratunga; Watts; Dmitrienko Tetrahedron Letters, 1991 , vol. 32, # 38 p. 5035 - 5038
Full Text: HTML
Citation Number: 15
Abstract
Abstract An FMO Theory prediction that 5-aminoindoles, 5, should react with electrophiles preferentially at C 4 rather than at C 6 whereas N 1-acyl-5-aminoindolines, 6, should react preferentially at C 6 rather than C 4 is borne out experimentally by the synthesis of a pyrrolo [3, 2-e] indole from 5 and pyrrolo [2, 3-f] indoles from 6.
Related Articles:
[Clentsmith, Guy K.B.; Field, Leslie D.; Messerle, Barbara A.; Shasha, Adelle; Turner, Peter Tetrahedron Letters, 2009 , vol. 50, # 13 p. 1469 - 1471]
[Berlin, A.; Bradamante, S.; Ferraccioli, R.; Pagani, G. A.; Sannicolo, F. Journal of the Chemical Society, Chemical Communications, 1987 , # 15 p. 1176 - 1177]