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Reactions of 6‐thiotheophylline with alkylating agents and epichlorohydrin: Isolation of S ‐alkylated 6‐thiotheophylline and 7‐(2,3‐thioepoxypropyl)theophylline
Author(s) -
Hayashi Hiroaki,
Suzuki Fumio,
Yasuzawa Toru,
Ueno Hideo
Publication year - 1993
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.5570300142
Subject(s) - epichlorohydrin , alkylation , chemistry , theophylline , organic chemistry , catalysis , pharmacology , medicine
Alkylation of 6‐thiotheophylline ( 1 ) under the aprotic basic condition affords S ‐alkylated 6‐thiotheophylline ( 3 ) together with an N 7 ‐alkylated product 4 . There is a tendency that the more reactive the alkylating agents are, the higher the yields of S ‐alkylated products are. On the other hand, treatment of 6‐thiotheophylline ( 1 ) with epichlorohydrin afforded an unexpected product, 7‐(2,3‐thioepoxypropyl)theophylline ( 6 ), neither an S ‐alkylated compound 3g nor an N 7 ‐alkylated compound 4g . The chemical structure was determined by nmr spectroscopic analysis.