Synthesis of 2-keto-1,4-diazacycloalkanes

Details Synthesis of 2-keto-1,4-diazacycloalkanes Synthesis of 2-keto-1,4-diazacycloalkanes

1981-07-18

1987-12-08

Berch, Mark L.

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

544347, 544348, 544349, 544354, 544384, 544295, C07D24144, C07D24118, C07D24138, C07D40308

Patent

active

047119578

ABSTRACT:
The disclosure deals with novel synthesis involving (a) hydrogenation of a cis-3,3-dialkyl-3,4-dihydroquinoxaline-2-one in the presence of a suitable hydrogenation catalyst, at elevated temperature and pressure, to yield a cis-3,3-dialkyl decahydroquinoxaline-2-one; (b) reaction of trans-1,2-diaminocyclohexane with acetone cyanohydrin in the presence of water to yield trans-3,3-dimethyl-decahydroquinoxaline-2-one; and (c) a reaction of 1,2-diamine with a saturated acyclic or cyclic monoketone or aldehyde and a holoform, in the presence of (i) a phase transfer catalyst (ii) an organic solvent, and (iii) solid or aqueous alkali to yield 2-keto-1,4-diazacycloalkanes. Such compounds exhibit exceptional UV light stabilizing property.

REFERENCES:
patent: 2920077 (1960-01-01), Bindler
patent: 4167512 (1979-09-01), Lai
patent: 4297497 (1981-10-01), Lai
Advanced Organic Chemistry (Mar.), 3rd Edition, pp. 310-312.
Gracian et al., J. Org. Chem., 36, 3989 (1971).
Brill et al., J. Org. Chem., 28, 1135 (1963).

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