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Pyrimidine derivatives. VII . Nucleophilic reactions of 5‐bromo‐1‐(bromoalkyl)‐6‐bromomethyl‐2,4(1 H ,3 H )‐pyrimidinediones
Author(s) -
Kinoshita Toshio,
Takaishi Yumiko,
Okunaka Tomoko,
Ohwada Takehiro,
Furukawa Sunao
Publication year - 1992
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.5570290410
Subject(s) - chemistry , sodium methoxide , morpholine , potassium thiocyanate , medicinal chemistry , bicyclic molecule , nucleophile , sodium azide , pyrimidine , azide , organic chemistry , stereochemistry , methanol , catalysis
The reactions of 1‐(bromoalkyl)‐5‐bromo‐6‐bromomethyl‐3‐methyl‐2,4(1 H ,3 H )‐pyrimidinedione (1) with several nucleophiles were examined as follows: by reaction with sodium methoxide, 6‐(bismethoxy)methyl‐5‐debrominated derivatives 2, 3 , and 4 were prepared; the corresponding di‐substituted compounds (side chains in 1‐and 6‐positions) 5, 6, 7 , and 9 were obtained by treatment with silver nitrate, silver acetate, potassium thiocyanate, and potassium thioacetate; the reaction with thioacetamide and iso ‐butylamine gave bicyclic compounds [1,4]thiazino[4,3‐c]‐ 11 , pyrazino[1,2‐ c ]‐ 12 , and [1,4]diazepino[1,2‐ c ]pyrimidinedione 13 , respectively; pyrrolidine, morpholine, and sodium azide afforded the corresponding 6‐substituted compounds 14, 15 , and 16 .