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Synthesis of certain alkenyl purines and purine analogs
Author(s) -
Sudhakar Rao T.,
Revankar Ganapathi R.
Publication year - 1995
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.5570320362
Subject(s) - chemistry , alkylation , purine metabolism , purine , dimethylformamide , pyrimidine , thiourea , stereochemistry , hydrolysis , sodium salt , derivative (finance) , organic chemistry , catalysis , financial economics , economics , solvent , enzyme , inorganic chemistry
Synthesis of alkenyl derivatives of certain purines and purine analogs is described. Direct alkylation of the sodium salt of 6‐chloropurine (1) either with 1‐bromo‐2‐pentene or 4‐bromo‐2‐methyl‐2‐butene in N , N ‐dimethylformamide furnished N‐7, 4a and N‐9, 3a , 3b alkenyl derivatives. Similar alkylation of 2‐amino‐6‐chloropurine (2) provided the corresponding N‐7, 4c‐4e and N‐9, 3c‐3e alkenyl derivatives. Acid hydrolysis of these chloro derivatives 3a‐3e, 4a,c‐e furnished the corresponding alkenyl hypoxan‐thines 6a, 6b and 7a or alkenyl guanines 6c‐6e and 7c‐7e. Treatment of 3a‐3d with thiourea in absolute ethanol provided the corresponding 6‐thio derivatives 5a‐5d. Alkylation of the sodium salt of either purine‐6‐carboxamide (8) or 1,2,4‐triazole‐3‐carboxamide (10) gave mainly one isomer 9a, 9b and 11a, 11b. The direct alkylation of pyrrolo[2,3‐ d ]pyrimidin‐4(3 H )‐one (12) gave N‐3 alkenyl derivatives 13a, 13b , and the N‐7 alkenyl derivatives 16a, 16b have been prepared starting from the 4‐chloro derivative 14 . Synthesis of 2‐amino‐7‐(2‐penten‐1‐yl)pyrrolo[2,3‐ d ]pyrimidin‐4(3 H )‐one (19a) has been accomplished starting from 2‐amino‐4‐methoxypyrrolo[2,3‐ d ]pyrimidine (17) . These alkenyl derivatives were found to be devoid of anti‐HCMV activity in vitro.