Synthesis of amino hydroxy cyclopentenones

Details Synthesis of amino hydroxy cyclopentenones Synthesis of amino hydroxy cyclopentenones

1980-12-30

1981-12-08

Doll, John

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

Organic compounds

Amino nitrogen containing

2604654, 556443, 560204, 562526, 564253, 564300, 564444, 564448, 568365, C07C 8500, C07C 8511, C07C 8524

Patent

active

043049346

ABSTRACT:
This invention relates to a method of synthesizing 3-amino-2-hydroxy-2-cyclopentenones possessing an aliphatic substituent in the 4-position which comprises reacting cyanoacetamide with an aliphatic aldehyde to yield the corresponding .beta.-substituted-.alpha.,.alpha.'-dicyanoglutaramide, hydrolyzing the amide to the corresponding .beta.-substituted glutaric acid, esterifying the acid to the corresponding dialkyl diester, converting the diester to a 1,2-bis(trimethylsiloxy)-4-substituted cyclopentene by reductive cyclization using chlorotrimethylsilane in the presence of sodium, hydrolyzing and oxidizing the bis(trimethylsiloxy) compound to the 2-hydroxy-4-substituted-2-cyclopentenone in the presence of a cupric salt, nitrosating the 2-cyclopentenone to the 2-hydroxy-4-substituted-5-oximino-2-cyclopentenone, converting the oxime to the 2-acetoxy-3-amino-4-substituted-2-cyclopentenone by reductive acetylation and removing the acetyl group by alkanolysis to yield the 3-amino-2-hydroxy-4-substituted-2-cyclopentenone product.

REFERENCES:
patent: 3690872 (1972-09-01), Gabrielsen et al.
Kent et al., "Organic Synthesis", vol. 3, pp. 591-593 (1955).
Ruhlmann, "Synthesis", No. 5, pp. 236-253 (1971).
Schrapler et al., "Chem. Ber.", 97, pp. 1383-1389 (1964).
Blomquist et al., "Organic Synthesis", vol. 4, pp. 838-839 (1963).
Murakami et al., "Chem. Ab.", vol. 47, AB. No. 2714h (1953).
Batesky et al., "J. Org. Chem.", vol. 24, pp. 1694-1695 (1959).

Affiliated with

Also associated with

Rating

Synthesis of amino hydroxy cyclopentenones does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of amino hydroxy cyclopentenones, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of amino hydroxy cyclopentenones will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-568887