Process for preparing hexahydroazepine, piperidine and pyrrolidi

Details Process for preparing hexahydroazepine, piperidine and pyrrolidi Process for preparing hexahydroazepine, piperidine and pyrrolidi

1980-06-23

1981-10-20

Bond, Robert T.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603265FL, 2603268, 546216, 546221, 546236, 546240, C07D22310

Patent

active

042960290

ABSTRACT:
2-Oxo-hexahydroazepine, -piperidine or pyrrolidines of formula ##STR1## wherein n is 2,3 or 4, R is hydrogen, lower alkyl, aryl(lower)alkyl, loweralkenylmethyl or cycloalkylmethyl, R.sup.1 is hydrogen or lower alkyl and R.sup.2 is hydrogen, lower alkyl or aryl(lower)alkyl are prepared by a novel process involving reaction of an anion of a lactam of formula ##STR2## where R.sup.3 is lower alkyl, aryl(lower)alkyl, trialkyl-, triaryl- or triarylalkyl-silyl with a benzyne of formula ##STR3## where R.sup.4 is lower alkyl, aryl(lower)alkyl or trialkyl-, triaryl- or triarylalkyl-silyl. The products are useful as intermediates for preparing pharmacologically active 2-unsubstituted -hexahydroazepine, -piperidine and pyrrolidine derivatives.

REFERENCES:
patent: 3729465 (1973-04-01), Cavalla et al.
patent: 4197239 (1980-04-01), Cavalla et al.
patent: 4197241 (1980-04-01), Cavalla et al.
Scardiglia and Roberts "Tetrahedron", vol. 3, pp. 197-208, (1958).
Duong et al. "Australian J. of Chemistry", (1976), vol. 29, pp. 2651-2665.
March "Advanced Organic Chemistry", McGraw-Hill, (1968), pp. 492-494.
Morrison et al. "Organic Chemistry", Third Edition, Allyn and Bacon, (1973), pp. 835-841.

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