Synthesis of 2-keto-1,4-diazacycloalkanes with a soft ion cataly

Details Synthesis of 2-keto-1,4-diazacycloalkanes with a soft ion cataly Synthesis of 2-keto-1,4-diazacycloalkanes with a soft ion cataly

1979-08-27

1981-01-20

Tovar, Jose

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

2602393R, 2602393B, C07D24108, C07D24308

Patent

active

042464129

ABSTRACT:
A phase transfer catalyzed "soft ion synthesis" is disclosed in which the presence of a "soft ion" generated in situ by a soft ion catalyst has a directive effect which favors the formation of a polysubstituted 2-keto-1,4-diazacycloalkane isomer having substituents on both N.sup.4 -adjacent carbon atoms ("C atoms") of its diaza ring; this isomer is formed at the expense of isomers in which an N.sup.4 -adjacent C atom is not substituted. Such an isomer which has substituents on each N.sup.4 -adjacent C atom is generally more effective as a u-v light stabilizer than an isomer which has an unsubstituted N.sup.4 -adjacent C atom, and therefore the former is more desirable.
A liquid phase reaction of an acyclic 1,2-diamine with a monoketone or monoaldehyde in the presence of a phase transfer catalyst, a haloform and alkali is disclosed, in which reaction a soft ion catalyst which generates a soft ion selected from the group consisting of cyanide, iodide and thiocyanate, has a directive effect on the reaction so as to produce more isomer with substituents on each N.sup.4 -adjacent C atom than would be formed, under identical conditions but without the presence of the soft ion. The directive effect of the soft ion appears to enhance any directive effect that a particular phase transfer catalyst may exhibit.

REFERENCES:
patent: 4167512 (1979-09-01), Lai
patent: 4190571 (1980-02-01), Lai et al.

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