Preparation of fused carbocyclic ring derivatives of pyridine

Details Preparation of fused carbocyclic ring derivatives of pyridine Preparation of fused carbocyclic ring derivatives of pyridine

1983-06-21

1985-09-03

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 93, 546104, 546108, 546112, 546176, 546 79, C07D21702, C07D21906, C07D22104, C07D22106

Patent

active

045394067

ABSTRACT:
An improved process for preparing fused carbocyclic ring derivatives of pyridine especially 5,6,7,8-tetrahydroquinoline 8-nitriles, amides and thioamides is described. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents. Typically a compound of formula A ##STR1## wherein M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted with a silyl compound R.sub.x.sup.a Si(NCY).sub.4-x III, wherein R.sup.a is selected from electron donating substituents, e.g. alkoxy or dialkylamino, and hydrocarbon substituents e.g. alkyl, at least one R.sup.a being an electron donating substituent, Y is oxygen or sulphur, x has a value from 1 to 3, then subjecting the product to hydrolysis or alcoholysis to obtain the corresponding nitrile, amide or thioamide, provided that when a nitrile is desired the molar ratio of compound III to compound A is at least 2:1 and x is 3 and Y is S. The products may be isolated as acid addition salts. Compound A may carry various substituents e.g. hydrocarbon substituents.
Some compounds of formula III are novel and are also claimed.

REFERENCES:
patent: 4000142 (1976-12-01), Curran et al.
patent: 4046895 (1977-09-01), Curran et al.
CA 71: 3085h, 8045e, (1969).
CA 67: 85521b, (1967).
CA 87: 68430s, (1977).
CA 86: 16786x, (1977).
Lettre, et al., Chem. Berichte, vol. 85, (1952), pp. 397-407.

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