132432-00-9Relevant academic research and scientific papers
AN UNUSUAL TERT-BUTYLAMINE MEDIATED CONVERSION OF 6-ARYL-7-FORMYL-2,4,5,8-TETRAHYDRO-1,3-DIOXA-5-AZOCINES TO 1,2,3,6-TETRAHYDROPYRIMIDINE DERIVATIVES
Stibranyi, Ladislav,Fisera, Lubor,Kacer, Rastislav,Oremus, Vladimir,Mihulova, Martina
, p. 2502 - 2509 (2007/10/02)
An unexpected contraction of the 8-membered ring to a 6-membered one occurring when 6-aryl-7-formyl-2,4,5,8-tetrahydro-1,3-dioxa-5-azocines II were treated with tert-butylamine afforded 4-aryl-5-formyl-1-(1,1-dimethylethyl)-1,2,3,6-tetrahydropyrimidines III.Reaction conditions for the photorearrangement of chlorophenyl-substituted condensed isoxazolines I to II were worked out.The reaction sequence: 1,3-dipolar cycloaddition, photochemical rearrangement, treatment with tert-butylamine constitutes a new route to pyrimidine derivatives from 2H,4H,7H-1,3-dioxepine.
