Spiroheterocyclic systems containing bridgehead nitrogen atom:synthesis,stereochemistry and antimicrobial activity of spiro(1'r)bicyclo [2.2.1] heptane-2',3-(4H)-[2H|-thiazolo [3,2-b]-s-tetrazines] and spiro [(1'r)-bicyclo [2.2.1] heptane-2',3-(4H)-[

摘要

The synthesis of(1'R)-6-arylspiro [bicyclo [2.2.1] heptane-2',3-(4H)-[2H]-thiazolo [3,2-b]-s-tetrazine] hydrobromide 2 and(1'R)-1,2,4,5-tetrahydro-1',7',7'-trimethylspiro [bicyclo [2.2.1] heptane-2',3-(2/-/)-thiazolo(3,2-6)-s-tetrazine]-6(7H)-one 3 have been accomplished by the reaction of(1 'R)-1,2,4,5-tetrahydro-1',7',7'-trimethylspiro [bicyclo [2.2.1] heptane-2',3-s-tetrazine]-6-thione 1 with a-haloketones and chloroacetic acid respectively.(1'R)-7-p-arylidene-1',7',7'-trimethylspiro(bicyclo [2.2.1] heptane 2',3-(4H)-[2H] thiazolo [3,2-d]-s-tetrazine]-6-(7H)-one 4 have been prepared either by the condensation of 3 with aldehydes or in a single-step by the reaction of 1 with ethyl chloroacetate and aldehydes in the presence of pyridine and piperidine.Condensation of 4 with 2,4-dinitrophenylhydrazine in the presence of anhyd sodium acetate furnishes(1'R)-8-(m-nitrophenyl)-7-(2",4"-dinitrophenyl)-c/s-8,8i-dihydrospiro [bicyclo [2.2.1] heptane-2',3-(4H)-[2H]-pyrazolo [3',4':4,5] thiazolo [3,2-b]-s-tetrazine] 5.The antibacterial and antifungal activities of some of the compounds have also been evaluated.