Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1979-04-30
1981-08-11
Daus, Donald G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
2602457, 2603265B, 26032637, 2603269, 2603435, 26034857, 26034858, 546223, 560226, 568484, 568495, C07D47114, C07D48704
Patent
active
042835364
ABSTRACT:
This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of among other alkaloids vincamine and other similar compounds possessing interesting psychopharmacologic properties.
A tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide a 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (III). Then compound (III) is reduced to give a 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into a chloroindolenine derivative (V) which is immediately treated with a metal dialkylmalonate such as thallium t-butyl methyl malonate to give a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into a alkyl 3-benzyl-1,2,3,4,5,6-hexahydro-(4,5-b) indole-5-carboxylate (VII). Compound (VII) is hydrogenated to give an alkyl 1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole 5-carboxylate (VIII). In an alternative embodiment, compound (VI) can be hydrogenated to the corresponding dialkyl 1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole-5,5-dicarboxylate which is then decarboxylated into compound (VIII). Compound (VIII) is condensed with a functionalised aldehyde, typically a epoxy aldehyde or a haloaldehyde such as 1-bromo-4-formylhexane, to give vincadifformine or similar pentacyclic derivatives.
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).
March, "Advanced Organic Chemistry", (1968), pp. 667, 668, 671.
Daus Donald G.
Rivers Diana G.
University of Vermont
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