Routes to HIV-integrase inhibitors: efficient synthesis of bicyclic pyrimidones by ring expansion or amination at a benzylic position

Ring expansion of [6,6] bicyclic pyrimidones led, through an aziridinium intermediate, to potent HIV-integrase inhibitors with a [7,6] core. A more flexible and diversity-oriented synthesis of functionalized pyrimidohexahydrodiazepines was then developed; the key benzylic substituent was introduced...

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Bibliographic Details
Published in:Tetrahedron letters 2009-01, Vol.50 (2), p.148-151
Main Authors: Ferreira, Maria del Rosario Rico, Cecere, Giuseppe, Pace, Paola, Summa, Vincenzo
Format: Article
Language:English
Subjects:
Aziridinium
DDQ
Pyrimidohexahydrodiazepines
Ring expansion
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Summary:Ring expansion of [6,6] bicyclic pyrimidones led, through an aziridinium intermediate, to potent HIV-integrase inhibitors with a [7,6] core. A more flexible and diversity-oriented synthesis of functionalized pyrimidohexahydrodiazepines was then developed; the key benzylic substituent was introduced in one pot by using sequentially DDQ and BnMeNH. Both synthetic routes are described.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.10.119