6-Halo-4-chromanamines useful as intermediates to make chiral hy

Details 6-Halo-4-chromanamines useful as intermediates to make chiral hy 6-Halo-4-chromanamines useful as intermediates to make chiral hy

1982-06-17

1983-12-06

Chan, Nicky

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D31102

Patent

active

044195214

ABSTRACT:
A novel process for the synthesis of chiral hydantoins of the structure ##STR1## wherein X is fluoro or chloro, from the corresponding 6-halo-4-chromanone of the structure ##STR2## is described. The compounds I are valuable in the treatment of certain chronic complications arising from diabetes mellitus. In addition the compound of the formula I wherein X is chloro possesses complementary hypoglycemic activity.
The process comprises the sequence of dehydrative coupling of the halochromanone (II) with S-(-)-alpha-methylbenzylamine to form the imine of structure ##STR3## addition of hydrogen cyanide to form the nitrile of structure ##STR4## condensation with chlorosulfonylisocyanate (or its equivalent) to form the alpha-methylbenzylhydantoin of structure ##STR5## and finally solvolysis of the latter to the chiral hydantoin of structure I.

REFERENCES:
patent: 4115407 (1978-09-01), Wright et al.
patent: 4117230 (1978-09-01), Sarges
patent: 4130714 (1978-12-01), Sarges

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