HIV REVERSE-TRANSCRIPTASE INHIBITORS - A CONCISE ENE REACTION-BASED SYNTHESIS OF THE 7,8-DIHYDRO-6H,12H-AZEPINO [2,1-B]QUINAZOLINE SYSTEM, AND ITS REACTION WITH NITRILE OXIDES

C GOULAOUIC-DUBOIS, D R ADAMS, A CHIARONI, C RICHE, F W FOWLER, D S GRIERSON

Research output: Contribution to journalArticle

Abstract

The reaction of amide (5), obtained in two steps from 2-amino benzophenone (4) with triflic anhydride, followed by treatment of the in situ generated imodyl triflate (7) with LiCN led to exclusive formation of the tetrahydroquinazoline (10). Thermolysis of this intermediate promoted an ene reaction leading to the azepino-quinazoline (11) (63% yield). The 1,3-dipolar cycloaddition between this product and nitrile oxide (12) proved chemoselective, producing the novel pentacyclic oxadiazine (14) as a 7:3 mixture of diastereomers in 79% yield.

Original languageEnglish
Pages (from-to)509-512
Number of pages4
JournalHeterocycles
Volume39
Issue number2
Publication statusPublished - 31 Dec 1994

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