3-Chloro-3-chlorosulfenyl-4′-methylspiro[chroman-2,1′-cyclohexane]-4-one (4) was prepared from the reaction of spiro 4′-methylcyclohexan-1′,2-chroman-4-one (3) with thionyl chloride according to re...

Chemical and anticancer activity studies for some 3-chloro-3-chlorosulfenyl-4′-methylspiro[chroman-2,1′-cyclohexane]-4-ones

2-(4-Fluorophenyl)methylidene-1-thiooxoindane-, 2-(4-methoxyphenyl) methylidene-1-thiooxoindane-, 2-(4-N,N-dimethyaminophenyl)methylidene-1-thiooxoindane dimers 5a–c were prepared by the reaction of the corresponding α,β -unsaturated ketones 3a–c with Lawesson' Reagent (LR) in refluxing benzene. When these dimers were refluxed with LR in xylene, the 1,2-thiaphospholene-2-sulfides 7a–c were obtained. On the other hand, the thermolysis of the dimers 5a–c in the presence of acrylamide or dichloromaleic anhydride gave the corresponding cycloadducts of Diels-Alder type 8a–c, and 10a–c, respectively. The 3-carbamoyl thiapyran derivatives 8a–c showed good antimicrobial activity.

[4 + 2] Cycloaddition Reactions Involving 2-Arylmethylidene-1-thiooxoindan Intermediates and Antimicrobial Activity Evaluation of Some Products

The very reactive α-oxo-thioketone derivatives 2a - d, generated via thermolysis of spirobenzopyran-3',2-[1,3,4]oxadithiino[5,6-c]benzopyran-4'-ones 1a - d, reacted with 2,3-dimethyl-1,3-butadiene and 1,3-cyclohexadiene under [4+2]-cycloaddition to afford spirobenzopyran-3',6-thiapyran-4'-one adducts 3a-d and spirobenzopyran-3',3-thiabicyclo[2.2.2]oct-5-en-4'-one adducts 4a-d, respectively. On the other hand, the reaction of α-oxo-thioketones 2a-d with isoprene afforded regioselectively only 3-methyl-thiapyran derivatives 5a-d. Single crystal X-ray diffraction studies of 4b, 4c, and 5a give a good support for the established structure.

Thermolysis of Some Spirobenzopyran-3′,2-[1,3,4]oxadithiino[5,6-c]benzopyran-4′-ones in the Presence of Some Homodienes and Crystallographic Studies of Some Adducts.

Bicyclic 6-6 Systems: Four Heteroatoms 1:3

Thermolysis of Some Spirobenzopyran-3’,2-[1,3,4]oxadithiino- [5,6-c]benzopyran-4’-ones in the Presence of Some Homodienes and Crystallographic Studies of Some Adducts

A. M. Moustafa

Papers

Thermolysis of Some Spirobenzopyran-3’,2-[1,3,4]oxadithiino- [5,6-c]benzopyran-4’-ones in the Presence of Some Homodienes and Crystallographic Studies of Some Adducts

Thermolysis of Some Spirobenzopyran-3′,2-[1,3,4]oxadithiino[5,6-c]benzopyran-4′-ones in the Presence of Some Homodienes and Crystallographic Studies of Some Adducts.