Synthesis and biological evaluation of the new ring system benzo[ f ]pyrimido[1,2- d ][1,2,3]triazolo[1,5- a ][1,4]diazepine and its cycloalkane and cycloalkene condensed analogues.

Derivatives of the new ring system benzo[ f ]pyrimido[1,2- d ][1,2,3]triazolo[1,5- a ][1,4]diazepinone and its cycloalkane and cycloalkene condensed analogues have been conveniently synthesized through a three-step reaction sequence. An atom-economical, one-pot, three-step cascade process engaging five reactive centers (amide, amine, carbonyl, azide, and alkyne) has been performed for the synthesis of alicyclic derivatives of quinazolinotriazolobenzodiazepine using cyclohexane, cyclohexene, and norbornene β-amino amides. The stereochemistry and relative configurations of the synthesized compounds were determined by 1D and 2D NMR spectroscopy and X-ray crystallography. The reaction was also performed using enantiomeric starting materials leading to enantiomeric quinazolinotriazolobenzodiazepine with an ee of 95%. The synthesis of 9 H -benzo[ f ]pyrimido[1,2- d ][1,2,3]triazolo[1,5- a ][1,4]diazepinone, a new heterocyclic system, was achieved in a good yield using a retro Diels-Alder (RDA) procedure. Some compounds were tested for antiproliferative activities against five human cancer cell lines of gynecological.