4995
Hala El-Minshawy Abd EL-Aziz Tolan
Studies on some New sulfur Ileterocyclic compounds with Expected Biological Activity.
Chroman-4-one, o-Chlorosulfenyl chlorides, o-Oxo thioketones,
11,3,4)oxadithiins, Nitrilimines, Thiadiazoles, Thiosulfines, lr,3,4,5,6loxatetrathiocins,
Il,2,4ltitJ7lolanes, 17,2,4,5ltetrathianes and Antiviral and anticancer
activities.
A series of new chroman-4-one derivatives have been synthesized starting from 3- chloro-3-chlorosulfenyl chlorides Za,b. Heating of 2a,b in chloroform with potassium iodide in acetonitrile gave the [1 ,3,Afoxadithiin derivatives 4a,b through formation of the u-oxo thioketone intermediate 3. Thiazolidine derivatives 6a-n were synthesized by the l,3-dipolar cycloaddition of nitrilimines generated in situ from hydrazonoyl chlorides 5a-g with the [1,3,4]oxadithiin derivatives 4a,b through cycloreversion of the latter compounds to o,-oxo thioketone intermediate 3. Compounds 2a,b (in KI, acetonitrile and acetone) and 4arb were treated with some dienes and the products obtained in each case (7a,b, 8a,b and garb) were found to be identical with the products from the corresponding reaction of 4arb with the same dienes (which presumably took place in both cases via formation of intermediate 3. Also' compounds2arb were treated with potassium cyanide, morpholine, or thiorcetic acid to give the 3-chloro-3-thiocyanato derivatives lla,b, 3-chloro-3- morpholinosulfenyl derivatives 13a,b or the 3-acetyldithio-3chloro derivatives 17arb,respectively. Also, compounds 12-16 were prepared from the reaction of sulfenyl chloride with other reagents. Thiosulfine intermediate lg which was liberated by treatment of lTarb with morpholine under mild conditions underwent disproportionation and cycloaddition , reactions to give a variety of products: [1,3,4]oxadithiin derivatives 4a,b, ll,3,4,5t,6loxatetrathiocin derivatives 20a,b, , fl,2,4,5ftetrathiane derivatives 2la,b ryfifl,Z,4ltrithiolane derivati ves2ka.b. The structures of the obtained products were confirmed by analytical and spectral measurements; besides anX-raydetermination was made for one compound (6a). Some of the newly prepared compounds were tested for antiviral and anticanceractivities.
2015
Ph.d
Minufyea
Science