The Stereochemistry of Organometallic Compounds. LXI. The Preparation of Quinazolines and Quinazolinones Involving Rhodium-Catalyzed Hydroformylation of Alkenyl Anilines

Abstract

Rhodium-catalysed reactions of ortho-alkenylaminobenzylamines or benzamides with H2/CO give quinazolines and quinazolinones containing a fused alicyclic ring in excellent yields. Reactions of N- allyl derivatives give a single regioisomer. Reactions of but-3-enyl analogues give readily separable mixtures of pyrrolo and pyrido derivatives. Their 3-methylbut-3-enyl analogues give the pyrido derivatives (12) and (13) in reactions which show unusual diastereoselectivity.