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Paper | Regular issue | Vol 36, No. 2, 1993, pp.259-280
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6008
Addition Reactions of 5-Aminobenzotriazoles with Dimethyl Acetylenedicarboxylate (DMAD). Formation of (Z/E) Michael Adducts, (Benzotriazol-5-yl)-2-pyridones, a Triazolo-9,10-dihydrobenzo[b]azepine and a Triazolo-2-oxindole

Paolo Sanna, Antonio Nuvole, Piera Attilia Sequi, and Giuseppe Paglietti*

*Instituto di Chimica Farmaceutica, University of Sassari, Via Muroni 23/a, 07100 Sassari, Italy


5-Aminobenzotriazoles (1a-d) reacted with DMAD to give the regioselective Michael adducts (Z)-(2a-d), accompanied with (benzotriazol-5-yl)-2-pyridones (3b-d), and in one case (2c) with the triazolo-9,10-dihydrobenzo[b]azepine (4). Cyclisation of the adducts (Z)-(2b-d) in Dowtherm gave the triazolo[4,5-f]quinolinones (6b-d), which were converted into chloro derivatives (9b-d), in trun hydrolysed and decarboxylated to 9-chloro-1(2)-methyltriazolo[4,5-f]quinolines (11c-d). Compound (1c) in refluxing acetonitrile with DMAD undergoes unusual cyclisation into triazolo-2-oxindole (5), then converted into 2-methyltriazolo[4,5-f]carbostyril-9-carboxylate (17).