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A new selective preparation of ethyl 7‐aminopteridine‐6‐ carboxylate derivatives and related compound
Author(s) -
Yamada Yoichi,
Yasuda Heinosuke,
Yoshihara Yuichi,
Yoshizawa Kazue
Publication year - 1999
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.5570360534
Subject(s) - chemistry , carboxylate , benzimidazole , vicinal , proton nmr , medicinal chemistry , organic chemistry , stereochemistry , combinatorial chemistry
A series of ethyl 7‐amino‐2,4‐dioxopteridine‐6‐carboxylates 4 and ethyl 7‐amino‐4‐oxo‐2‐thioxopteridine‐6‐carboxylates 5 , of interest biologically, has been prepared in one step from the reaction of such vicinal ‐diamines as 1,3‐dialkyl‐5,6‐diaminouracils 2 or 1,3‐dialkyl‐5,6‐diamino‐2‐thiouracils 3 with diethyl ( E )‐2,3‐dicyanobutenedioate ( 1 ). Moreover, ethyl 3‐amino[1,2,4]triazino[2,3‐ a ]‐1 H ‐benzimidazole‐2‐carboxylate ( 11 ) was also obtained from the reaction between 1,2‐diamino‐1 H ‐benzimidazole ( 10 ) and 1 . The structural studies of 4, 5 , and 11 prepared were carried out by nmr experiments in some details.