Premium
A novel synthesis of theophylline derivatives
Author(s) -
Yoneda Fumio,
Koga Ryosuke
Publication year - 1982
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.5570190421
Subject(s) - chemistry , substituent , theophylline , hydrochloric acid , acetic acid , adduct , medicinal chemistry , purine , organic chemistry , enzyme , medicine , endocrinology
Treatment of 6‐amino‐5‐arylazo‐1,3‐dimethyluracils with ethyl propiolate gave the corresponding Michael‐type adducts, 5‐arylazo‐1,3‐dimethyl‐6‐ethoxycarbonylvinylaminouracils, which on treatment with a mixture of hydrochloric acid and acetic acid caused the acid‐catalyzed rearrangement accompanied with rearrangement to give rise to the corresponding 8‐anilinomethyltheophylline derivatives. In the case that the arylazo group possesses an electron‐releasing substituent such as methoxy, the reaction proceeded in a different way to afford 1,2‐bis(theophyllin‐8‐yl)ethane. The presumable reaction mechanisms for the above purine syntheses were proposed.