Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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


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.