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Annelated piperazinyl‐7,8‐dihydro‐6 H ‐thiopyrano[3,2‐ d ]pyrimidines
Author(s) -
Wu M. T.,
MacCoss M.,
Ikeler T. J.,
Hirshfield J.,
Arison B. H.,
Tolman R. L.
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270607
Subject(s) - chemistry , tricyclic , pyrimidine , stereochemistry , tetrahydropyran , ring (chemistry) , condensation , medicinal chemistry , organic chemistry , physics , thermodynamics
Tricyclic analogs of piperazinylthiopyrano[3,2‐ d ]pyrimidine hypoglycemic agents were prepared. The angular tricyclic systems, 8,9‐dihydro‐7 H ‐thiopyrano[2,3‐ e ][1,2,4]triazolo[4,3‐ a ]pyrimidine and 8,9‐dihydro‐7 H ‐tetrazolo[1,5‐ a ]thiopyrano[2,3‐ e ]pyrimidine derivatives were synthesized from 2,4‐dichloro‐7,8‐dihydro‐6 H ‐thiopyrano[3,2‐ d ]pyrimidine in three step sequences. Derivatives of the linear tricyclic system, 5,6‐dihydro‐7 H ‐thiopyrano[3,2‐ d ][1,2,4]triazolo[2,3‐ a ]pyrimidine, were prepared by condensation of 3‐amino‐1,2,4‐triazole with ethyl 3‐oxo‐tetrahydropyran‐2‐carboxylate. The tricyclic heteroaryl‐piperazines lacked significant hypoglycemic activity.