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The facile Diels-Alder cycloaddition reactions of four enantiopure (RS)-[(1S)-isoborneol-10sulfinyl]-substituted dienes 1a–d with 4-phenyl-1,2,4-triazoline-3,5-dione (2) are reported. The cycloadducts 3a,b were obtained in enantiopure form and good yields. The (RS)-7-[(1S)isoborneol-10-sulfinyl]-substituted (5S)-5,8-dihydro-5-methoxy-2-phenyl[1,2,4]triazolo[1,2a]pyridazine-1,3(2H)-dione (3a) features the pyridazine scaffold of azafagomines and their analogues, which are potent inhibitors of various glycosidases; (RS)-6-[(1S)-isoborneol-10sulfinyl]-2-phenyl[1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-diones 3b–d and 4c,d, are closely related to fully aromatic cinnolines and their saturated and partially saturated derivatives whose biological activity has been widely recognized.

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Synthesis of enantiomerically pure, partly saturated (RS)-[(1S)-isoborneol-10-sulfinyl]-substituted [1,2,4]triazolo[1,2-a]pyridazine, cinnolines and benzo[f]cinnolines