Method for preparing 8-acylthio-1,2,3,4,5,6-hexahydro-2,6-methan

Details Method for preparing 8-acylthio-1,2,3,4,5,6-hexahydro-2,6-methan Method for preparing 8-acylthio-1,2,3,4,5,6-hexahydro-2,6-methan

1983-05-19

1985-09-17

Schwartz, Richard A.

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

544333, 546 97, C07D40112, C07D22126

Patent

active

045422150

ABSTRACT:
A method for preparing 8-acylthio-1,2,3,4,5,6-hexahydro-2,6-methano-3,6(e),11(a)-trimethyl-3-benz azocines represented by general formula (I) below ##STR1## wherein R represents an alkyl group, a phenyl group or a heterocyclic group, which comprises reacting 1,2,3,4,5,6-hexahydro-2,6-methano-3,6(e),11(a)-trimethyl-3-benzazocine represented by the formula (II) below ##STR2## or its salt with chlorosulfonic acid, heating the reaction product in the presence of a reducing agent, and reacting the reaction mixture with an acyl halide represented by the general formula (III)

REFERENCES:
Jacobson, A., et al., J. Med. Chem., 8(5), 563 (1965).
March, J., Advanced Organic Chemistry, McGraw Hill, New York, 1968, pp. 402 and 901.
Chemical Abstracts, 90:22526m (1979) [Demoute, J., et al., J. Chem. Res. (5)1978, (7), 244-5].
Shiotani, S., et al., Chem. Pharm. Bull. (Japan), 20(2), 277-283 (1972).
Bordwell, F., et al., J. Am. Chem. Soc., 73, 2251 (1951).
Hori, M., et al., Heterocycles, 20(12), 2359 (1983).
Bottino, F., et al., J. Org. Chem., 46(13), 2793 (1981).

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