Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1978-08-24
1981-05-12
Daus, Donald G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
2602457, 2603265B, 2603269, 2603435, 26034857, 26034858, 26032637, 546223, 560226, 568484, 568495, C07D47114, C07D48704
Patent
active
042673305
ABSTRACT:
This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of vincamine and other related compounds possessing interesting psychopharmacologic properties.
A N-benzyl-tetrahydro-.gamma.-carboline compound (III) is halogenated with t-butyl hypochlorite to obtain a haloindolenine compound which is directly treated with a metal dialkyl malonate such as thallium dialkyl malonate to provide a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5,5-dicarboxylate compound, said latter compound being hydrogenated to provide a dialkyl 1,2,3,4,5,6 hexahydroazepino (4,5-b) indole-5,5-dicarboxylate, said latter compound being condensed with a functionalized aldehyde, typically a haloaldehyde, to provide vincadifformine or a related derivative by passing through an intermediate compound being a salt of a dialkyl 3,3-(alkenyl)-1,2,3,4,5,6-hexahydroazepino(4,5-b) indolinium-(5,5)-dicarboxylate.
REFERENCES:
patent: 3525750 (1970-08-01), Renner
patent: 4146643 (1979-03-01), Pfaffli
patent: 4154943 (1979-05-01), Kuehne
patent: 4220774 (1980-09-01), Kuehne
Kuehne et al., (I), J. Org. Chem., vol. 43, No. 19, pp. 3702-3704 (9/15/78).
Kuehne et al., (II), J. Org. Chem., vol. 43, No. 19, pp. 3705-3710 (9/15/78).
Kuehne et al., (III), J. Org. Chem., vol. 44, No. 7, pp. 1063-1068 (3/30/79).
Wang, Dissertation Abstracts, vol. 26, (3), p. 1361 (1965).
Kutney et al., J.A.C.S. 90, 3891 (1968).
Daus Donald G.
Omnium Chimique Societe Anonyme
Rivers Diana G.
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