Reaction of a variety of 6-arylmethylene-6,7,8,9-tetrahydro-5H-benzocycloheptene-5-ones 1a–f with nitrilimines (generated in situ by triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides 2) in refluxing benzene, afforded the corresponding spiro[benzocycloheptene-6(5H),3′-[3H]pyrazol]-5-ones 3a–h and not the isomeric forms spiro[benzocycloheptene-6(5H),4′-[4H]pyrazol]-5-ones 4 in a highly regioselective manner. The stereochemical configuration of the isolated products was established to be 3′R, 4′S based on single crystal X-ray diffraction of 3a.
GaoX.C., CaoH., ZhangL. Q., ZhangB. W., CaoY., and HuangC. H., J. Mater. Chem., 1999, 9, 1077.
33.
(a) AnelliP.L., and CroceP. D., Gazz. Chim. Ital., 1981, 111, 269.
34.
AbdallahM.A., AlbarH. A., and ShawaliA. S., J. Chem. Res. (S), 1993, 182.
35.
GirgisA.S., Z. Naturforsch., 2000, 55b, 222.
36.
FathiT., CiamalaK., DinhAn N., and VebreJ., Can. J. Chem., 1994, 72, 1424.
37.
CCDC 274948 contains the supplementary crystallographic data for this paper. They can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request.cif.
38.
AltomareA., CascaranoG., GiacovazzoC., GuagliardiA., BurlaM. C., PolidoriG., and CamalliM., J. Appl. Cryst., 1994, 27, 435.
39.
MackayS., GilmoreC. J., EdwardsC., StewartN., and ShanklandK., maXus Computer Program for the Solution and Refinement of Crystal Structure. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow (1999).
40.
(a) El-RayyesN.R., and RamadanH. M., J. Heterocycl. Chem., 1987, 24, 589.
41.
Buu-HoiNg. Ph., XuongN. D., and RipsR., J. Org. Chem., 1957, 22, 193.
42.
OrlovV.D., SurovYu. N., MikhedkinaE. I., Nodel'manO. A., BazavlukA. D., and LavrushinV. F., Org. React. (Tartu), 1984, 21, 363.
