Synthesis, structure and some reactions of 4a ',5 ',6 ',7,8 ',8a '-hexahydro-4 ' H-spiro[cyclohexane-1,9 '-[1,2,4]triazolo[5,1-b]-quinazolines]

摘要

2'-Substituted 5',6',7',8'-tetrahydro-4'H-spiro[cyclohexane-1,9'-[1,2,4]triazolo[5,1-b]quinazolines] 3a-d were synthesized by condensation of 3-substituted 5-amino-1,2,4-triazoles 1a-d with 2-cyclohexylidene cyclohexanone 2 in DMF. The compounds 3 were hydrogenated with sodium borohydride in ethanol to give 2'-substituted cis-4a',5',6',7',8',8 a'-hexahydro-4'H-spiro[cyclohexane-1,9'-[1,2,4]triazolo[5,1-b]quinazolines] 4a-d in high yields. The reactions of alkylation, acylation and sulfonylation of the compounds 4 were studied. The structure of the synthesized compounds was determined on the basis of NMR measurements including HSQC, HMBC, NOESY techniques and confirmed by the X-ray analysis of 6 and 11b. The described synthetic protocols provide rapid access to novel and diversely substituted hydrogenated [1,2,4]triazolo[5,1-b]quinazolines.