S. Gupta et Sn. Rastogi, SYNTHESIS AND STEREOCHEMISTRY OF 2-ACETYL-3-PHENYLCYCLOALKA[C]PYRAZOLINES, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 34(3), 1995, pp. 245-247
Condensation of 2-phenylmethylene-1-cyclo-hexanone/heptanone (4/5) and
2,6-bisphenylmethylene-1-cyclohexanone (7) with hydrazine hydrate in
acetic acid gives two diastereoisomers of 2-acetyl-3-phenylcyclo-hexa/
hepta[c]-pyrazolines (8a,b/9a,b) and 7-phenylmethylene-cyclohexa[c]-py
razolines (11a,b), respectively while corresponding 2-phenylmethylene-
1-cyclooctanone (6) furnishes only one diastereoisomer of 2-acetyl-3-p
henylcycloocta[c]pyrazoline (10). The trans-isomers (8a-11a), which ar
e produced in major amount, fail to prevent pregnancy in female albino
rats at 10 mg/kg dose.