Process for the preparation of 1-alkylisoquinoline derivatives

Details Process for the preparation of 1-alkylisoquinoline derivatives Process for the preparation of 1-alkylisoquinoline derivatives

1991-08-12

1993-12-21

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 14, 546 90, C07D21724

Patent

active

052722708

ABSTRACT:
The invention relates to a process for the preparation of 1-alkyl-1,2,3,4-tetrahydroisoquinoline derivatives of the general formula ##STR1## The compounds can be used for the preparation of tetrahydroisoquinolines of the reticuline type, or of the norreticuline type, by reductive removal of the OH groups or, if they carry an acyl protective group on the nitrogen, for the preparation of isoquinolines of the papaverine type by acid-catalyzed hydrolysis with removal of the acyl groups and simultaneous removal of the hydroxyl groups.
These 1-alkyl-1,2-dihydroisoquinoline derivatives can then be used for the preparation of isoquinolines of the papaverine type by aromatization by means of acids or hydrazine.

REFERENCES:
patent: 3452010 (1966-08-01), Pohlke et al.
patent: 4757078 (1988-07-01), Misra
patent: 4843077 (1989-06-01), Hinkle et al.
S. F. Dyke et al., Tetrahedon, vol. 22, pp. 3803 et seq. (1971).
K. Yamada et al., Chem. Pharm. Bulletin, vol. 30, pp. 3197 et seq. (1982).
G. Blasko et al., The Alkaloids, Academic Press, Inc., vol. 31, pp. 1, et seq. (1987).
A. I. Meyers et al., Heterocycles, vol. 28, pp. 295, et seq. (1989).
Wei Zhang et al., Journal of American Chemical Society, vol. 112, pp. 2801 et seq. (1990).
E. N. Jacobsen et al., Journal of American Chemical Society, vol. 110, pp. 1968 et seq. (1988).
B. M. Kim et al., Tetrahedon Letters, vol. 30, pp. 655 et seq. (1989).
D. Seebach et al., Helv. Chim. Acta, vol. 70, pp. 1357 et seq. (1987).
Yun He et al., Synthetic Communications, vol. 19, pp. 3051 et seq. (1989).
Chemical Abstracts 108, No. 9, Feb. 29, 1988, "The synthesis of the isoquinoline alkaloid calycotomine", p. 711, Lenz G.
Chemical Abstracts 98, No. 9, Feb. 28, 1983, Yamada K. et al., "Studies on 1,2,3,4-tetrahydroisoquinolines", p. 665.

Affiliated with

Also associated with

Rating

Process for the preparation of 1-alkylisoquinoline derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the preparation of 1-alkylisoquinoline derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of 1-alkylisoquinoline derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-310194