DIBORANE AS A REDUCING AGENT - IX - REDUCTION OF A TRIS (TRIFLUOROACETYL)ENAMINOSPIROINDOLINE

Authors
BISWAS KM MALLIK H HALDER S
Citation
Km. Biswas et al., DIBORANE AS A REDUCING AGENT - IX - REDUCTION OF A TRIS (TRIFLUOROACETYL)ENAMINOSPIROINDOLINE, Monatshefte fuer Chemie, 128(12), 1997, pp. 1283-1289
Citations number
15
Categorie Soggetti
Chemistry
Journal title
Monatshefte fuer Chemie → ACNP
ISSN journal
00269247
Volume
128
Issue
12
Year of publication
1997
Pages
1283 - 1289
Database
ISI
SICI code
0026-9247(1997)128:12<1283:DAARA->2.0.ZU;2-V
Abstract
Reduction of the title compound (2) with diborane furnishes -3-(2'-(tr ifluoroethylamino)ethyl)-3-vinylindoline (4), uoroethyl-3-(2'-(trifluo roethylamino)-ethyl)indole (5), and 2-trifluoroethyl-1,2,3,4-tetrahydr o-beta-carboline (6). However, treatment of 2 with lithium aluminum hy dride, H-2/Pd on charcoal, and sodium borohydride affords hydroxyspiro indolenine 8, hydroxy-bis(trifluoroacetyl)enaminospiroindoline 9, and N-ethyltryptamine 7, respectively. The results are discussed and the m echanisms of the reactions leading to 4-8 are presented.