METHODS FOR PRODUCTION OF RACEMIC AMINOSUBSTITUTED 5,6,7,8-TETRAHYDROQUINOLINE OR RACEMIC AMINOSUBSTITUTED 5,6,7,8-TETRAHYDROISOQUINOLINE, METHODS FOR SEPARATION AND RACEMIZATION THEREOF, METHODS FOR PRODUCTION OF KETOSUBSTITUTED 5,6,7,8-TETRAHYDROQUINOLINE OR KETOSUBSTITUTED 5,6,7,8-TETRAHYDROISOQUINOLINE, METHOD FOR PRODUCTION OF ENANTIOMER PF CONDENSED BYCYCLIC RING SUBSTITUTED WITH PRIMARY AMINE, 5,6,7,8-TETRAHYDROQUINOLINE DERIVATIVES

摘要

FIELD: organic chemistry, in particular methods for production and separation of racemic aminosubstituted condensed bycyclic ring systems.;SUBSTANCE: in one embodiment claimed method includes selective hydration of aminosubstituted aminosubstituted condensed aromatic ring system. In alternative embodiment claimed method includes preparation of racemic aminosubstituted condensed bycyclic ring system by nitrozation. Moreover invention relates to enzymatic resolution of racemic mixture to produce (R)- and (S)-forms of aminosubstituted condensed bycyclic rings as well as to racemization method for secondary preparation of non-preferable enantiomer. Also disclosed is method for production of enantiomer of condensed bycyclic ring substituted with primary amine by preparation of respective enantiomerically pure imine of condensed bycyclic ring, diastereoselective reducing thereof and elimination of auxiliary chiral fragment. In abovementioned processes compounds of formulae I, II, III, IV, V, VI, VII, VIII, XIII, XIX which are described in specification together with radical meanings. Moreover invention relates to 5,6,7,8-tetrahydroquinoline derivatives such as N-(2-methyl-5,6,7,8-tetrahydroquinolin-4-yl)-acetamide, N-(1,2,3,4-tetrahydroquinolin-7-yl)-acetamide, (R,S)-N-(2-methyl-5,6,7,8-tetrahydroquinolin-8-yl)-acetamide, etc.;EFFECT: effective methods for production of racemates and enantiomers of various ring systems.;44 cl, 37 ex, 2 tbl