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Synthesis of indole and indolenine derivatives starting from indoline‐2‐thiones
Author(s) -
Nishio Takehiko,
Saku Osamu,
Yamamoto Hiroshi
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380115
Subject(s) - indoline , chemistry , triphenylphosphine , indole test , ketone , halo , organic chemistry , thiourea , medicinal chemistry , catalysis , physics , quantum mechanics , galaxy
Indoline‐2‐thiones 1a‐b,d,f,h , which have at least one hydrogen at the 3‐position reacted with α‐halo ester 2a‐d , α‐halo ketones 2e‐f , and a‐bromoacetonitrile 2g to give 2‐alkylthioindole derivatives 3–11 . In a similar manner treatment of 3,3‐disubstituted indoline‐2‐thiones 1c,e with α‐halo esters 2a,c,d and α‐halo ketone 2e gave 2‐alkylthioindolenines 12–16 . Treatment of 1,3,3‐ trisubstituted indoline‐2‐thiones 1g,i with ethyl bromo‐acetate 2a resulted in recovery of starting materials. Desulfurization of indolenine 14 with triphenylphosphine gave 2‐alkylideneindoline 19 .