[4 + 2] Cycloaddition reaction of C-aryl ketenimines with PTAD as a synthetic equivalent of dinitrogen. Synthesis of triazolocinnolines and cinnolines.
C,C,N-Triaryl ketenimines and C-alkyl-C,N-diaryl ketenimines react with 2 equiv of PTAD to provide 1,2,4-triazolo[1,2-a]cinnolines with a pendant triazolidindione group by means of a Diels-Alder/ene sequence. The treatment of such adducts with potassium hydroxide affords 3-aminocinnolines.
Alajarin
Mateo
M
Departamento de Quimica Organica, Facultad de Quimica, Universidad de Murcia, Campus de Espinardo, 30100 Murcia, Spain. alajarin@um.es
Bonillo
Baltasar
B
Marin-Luna
Marta
M
Vidal
Angel
A
Orenes
Raul-Angel
RA