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Communication | Regular issue | Vol 12, No. 11, 1979, pp.1433-1438
Published online, 1st January, 1970
DOI: 10.3987/R-1979-11-1433
Quinazolinocarboline Alkaloids Chemistry: Thermal Rearrangement of 14-Alkylindole[2’,3’:3,4]pyrido[2,1-b]quinazolin-5-one. Part II

Bruno Danieli, Giordano Lesma, and Giovanni Palmisano*

*Instituto Chimica Industriale, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

Abstract

The thermal rearrangement of 14-alkylindolo[2’,3’:3,4]pyrido[2,1-b]quinazolin-5-ones (1a-h) in boiling DMSO has been studied. (1a-d,f,g) give hydrogen migration products (2a,c,e,g,h) and alkyl migration products (2b,d,f,k,l) respectively, whereas (1e,h) give only (2g). Crossover experiments support the intramolecular character of these processes. The formation of hydrogen migration products is interpreted through an α-elimination induced by N13 atom and α-bond cleavage. A radical fragmentation-recombination mechanism is suggested for alkyl migration.