The facile Diels-Alder cycloaddition reactions of four enantiopure (RS)-[(1S)-isoborneol-10-sulfinyl]-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[1,2-a]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-10-sulfinyl]-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.

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

AVERSA, Maria Chiara;BARATTUCCI, Anna;BONACCORSI, Paola Maria;GIANNETTO, Placido
2004-01-01

Abstract

The facile Diels-Alder cycloaddition reactions of four enantiopure (RS)-[(1S)-isoborneol-10-sulfinyl]-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[1,2-a]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-10-sulfinyl]-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.
2004
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11570/1890255
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