Palladium-catalysed carbonylation of 4-substituted 2-iodoaniline derivatives:: carbonylative cyclisation and aminocarbonylation

2-Iodoaniline derivatives were used as bifunctional substrates in palladium-catalysed carborylation. Depending on the substituents, two types of compounds were synthesised: having methyl or hydrogen in 4-position 2-aryl-benzo[d][1,3]oxazin-4-one derivatives have been formed, chloro, bromo, cyano or nitro groups in the same position resulted in the formation of dibenzo[b,f][1,5]-diazoeine-6,12-dione derivatives. In the presence of various primary and secondary amines (tert-butylamine, amino acid methyl esters) as N-nucleophiles 2-keto-carboxamides were obtained as major products in aminocarbonylation reaction with double carbon monoxide insertion. (c) 2006 Elsevier Ltd. All rights reserved.