Preparation of tetrahydroquinolines and related compounds

Details Preparation of tetrahydroquinolines and related compounds Preparation of tetrahydroquinolines and related compounds

1983-06-21

1985-07-02

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 93, 546102, 546104, 546176, 546 79, C07D21516, C07D21904, C07D22106, C07D22116

Patent

active

045269700

ABSTRACT:
An improved process for preparing tetrahydroquinolines and related compounds 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## where M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted, e.g., in an ether solvent, with a silyl compound R.sub.x.sup.a Si(NCY).sub.4-x (III) wherein R.sup.a is alkyl, cycloalkyl, aralkyl, or aryl, at least one group R.sup.a being a branched chain alkyl, cycloalkyl, aryl or branched chain aralkyl, 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 obtained as acid addition salts.
Compound A may contain various substituents, e.g., hydrocarbon substituents. Some compounds of formula III are novel and are also claimed.

REFERENCES:
patent: 4000278 (1976-12-01), Curran
patent: 4085108 (1978-04-01), Curran et al.
CA 95:81085t.
CA 96:6242j (1982).
CA 81:153382y (1974).
CA 90:87566u (1979).
Chem. Abstracts, vol. 83, (1975), p. 473, Abstract No. 27828b.
Chem. Abstracts, vol. 85, (1976), p. 506, Abstract No. 46340u.

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