Substituted indanones

Details Substituted indanones Substituted indanones

1976-07-14

1977-11-22

Myers, Jane S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C14368

Patent

active

040596125

ABSTRACT:
Total synthesis of known progestationally active steroidal materials. The steroids can be synthesized depending on the particular starting reactants selected by employing as intermediates bicyclic compounds of the formula ##STR1## WHEREIN M IS AN INTEGER HAVING A VALUE OF 1 OR 2; R.sub.4 is hydrogen or lower alkyl; Z is lower alkylenedioxy, CH(OR.sub.2) and carbonyl; R.sub.8 when taken alone is hydrogen; R.sub.9 when taken alone is lower alkoxy-carbonyl, aryloxy-carbonyl, lower cycloalkyloxy-carbonyl, carbonyl-halide, hydrogen, carboxy, formyl and methylene-X, where X is a leaving group and when taken together are methylene; with the proviso that when Z is carbonyl R.sub.8 when taken alone is hydrogen; R.sub.9 when taken alone is carbonyl halide, hydrogen, carboxy, formyl and methylene-X where X is a leaving group and when taken together are methylene and R.sub.2 is hydrogen, lower alkyl, lower alkoxy-lower alkyl, phenyl-lower alkyl, tetrahydropyranyl, lower alkanoyl, benzoyl, nitrobenzoyl, carboxy-lower alkanoyl, carboxybenzoyl, trifluoroacetyl and camphorsulfonyl
And reacting them in the case where R.sub.8 and R.sub.9 taken together are methylene or R.sub.8 is hydrogen and R.sub.9 is methylene-X with .beta.-keto esters and other analogs of the formula ##STR2## wherein R.sub.6 is selected from the group consisting of ##STR3## and lower alkyl; R.sub.7 is lower alkyl; R.sub.15 is selected from the group consisting of oxo, lower alkylenedioxy or (hydrogen and lower alkoxy); B is selected from the group consisting of lower alkoxy-carbonyl-methylene, lower-aryloxy-carbonyl-methylene, cyanomethylene, lower alkyl sulfinyl-methylene, lower alkyl sulfonyl-methylene, and R.sub.25 and R.sub.26 are independently selected from the group consisting of hydrogen, hydroxyl and lower alkyl.

REFERENCES:
patent: 3478062 (1969-11-01), Amiard et al.
patent: 3616228 (1971-10-01), Schubert et al.
patent: 3639428 (1972-02-01), Fried
patent: 3859309 (1975-01-01), Fried
patent: 3925478 (1975-12-01), Hajos

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