Thiohydrazoazetidinones

Details Thiohydrazoazetidinones Thiohydrazoazetidinones

1977-05-16

1979-03-06

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07D20508

Patent

active

041430379

ABSTRACT:
A process is disclosed for preparing compounds of structure: ##STR1## where R.sup.1 is hydroxyl, alkoxy with 1 to 4 carbon atoms, trichloroethoxy, benzyloxy, p-methoxybenzyloxy, p-nitrobenzyloxy, benzhydryloxy, triphenylmethoxy, phenacyloxy, or p-halophenacyloxy;
Z is hydrogen, hydroxyl, --O-alkyl, --O--CO-alkyl, --Br, --I, --N.sub.3, --O--CO--CH.sub.3, O--CO--NH.sub.2, or an S-mononuclear heterocyclic ring,
Starting from ##STR2## where R is hydrogen, alkyl having from 1 to 4 carbon atoms, cyano-methyl, thienyl-methyl, furyl-methyl, naphthyl-methyl, phenyl-methyl, phenoxy-methyl, phenyl-isopropyl, phenoxy-isopropyl, pyridyl-4-thiomethyl, or tetrazolyl-1-methyl;
R.sup.2 and R.sup.3 are lower alkyl, a mononuclear aryl ring, CN, a mononuclear heterocyclic ring or the radicals --COR.sup.4, --COOR.sup.4, ##STR3## --CONHR.sup.4, or R.sub.2 and R.sub.3 together represent ##STR4## where T represents ##STR5## and R.sup.4 is a lower alkyl, a mononuclear aryl or heterocyclic ring, WHEREIN THE COMPOUND (II') is reacted with a phosphorous halide in the presence of a tertiary amine, the corresponding imino chloride is reacted with a lower aliphatic alcohol, the iminoether so formed is hydrolyzed in an acid medium, and the resultant 3-amino-2-.beta.-thiohydrazoazetidinone: ##STR6## in which R.sup.1, R.sup.2, R.sup.3 and Z have the meanings given heretofore,
Is reacted between -100.degree. and +120.degree. C. with inorganic basic or weakly acid oxides or inorganic and organic bases, to give (V).

REFERENCES:
patent: 4036835 (1977-07-01), Foglio et al.
Linke et al., Chem. Abs. 74, 64123c (1971).

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