Process for the preparation of 6-(3,4-dihydro-3-oxo-1,4(2H)-benz

Details Process for the preparation of 6-(3,4-dihydro-3-oxo-1,4(2H)-benz Process for the preparation of 6-(3,4-dihydro-3-oxo-1,4(2H)-benz

1990-12-21

1993-06-22

Tsang, Cecilia

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

Organic compounds

Chalcogen in the nitrogen containing substituent

C07D41302, C07D41310

Patent

active

052217426

ABSTRACT:
The invention relates to a process for the synthesis of compounds of the formula I ##STR1## wherein R.sub.1 -R.sub.5 are as defined herein. The process is a multistep process which comprises acylating a 2-benzoxazolinone with an alkanoic anhydride to form an acylated carbamate, hydrolyzing the carbamate, reacting the resultant aminophenol with haloalkanoyl halide to form a substituted benzoxazine, reacting the benzoxazine with an aldehyde, alkylating the resultant aminomethyl compound with an alkylating agent to form a quaternary ammonium salt, reacting the salt with an alkali metal cyanide to form a nitrile, hydrolyzing the nitrile and reacting the resultant carboxylic acid with hydrazine.
The compounds are useful as cardiotonic and vasodilating agents and as inhibitors of phosphodiesterase fraction III and platelet aggregation. In addition, the compounds are active as smooth muscle relaxants and bronchodilators.

REFERENCES:
patent: 4721784 (1988-01-01), Combs
patent: 4766118 (1988-08-01), Combs
Bonte, et al, Eur. J. Med. Chem., 9, pp. 497-500 (1974).
Moussavi et al., Eur. J. Med. Chem., 24, pp. 55-60 (1989).
McEvoy et al., J. Org. Chem., 38, No. 23, pp. 4044-4048 (1973).
Combs et al., J. Med. Chem., 33, pp. 380-386 (1990).
Sastry et al., Chemical Abstracts vol. 112, No. 198278u (1989).

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