| A variety of mixed atom heterocycle compounds have been synthetized. Most of the syntheses presented are novel and contribute to a new methodology.; Chapter 2. We investigated the use of new benzotriazole reagent, 2-benzotriazolyl-1,3-dioxolane, as a remarkably stable and versatile electrophilic formylating reagent. We report the use of 2-benzotriazolyl-1,3dioxolane for the direct electrophilic introduction of a masked aldehyde moiety under very mild conditions.; Chapter 3. The synthesis of N-acylbenzotriazole derivatives from 2-benzotriazolyl-1,3-oxathiolane is reported. We propose 2-benzotriazolyl-1,3-oxathiolane as an acyl carbanion equivalent reagent for the direct nucleophilic introduction of a carbonyl moiety.; Chapter 4. 2-Alkylthio-substituted benzoquinones were prepared from benzoquinone and mercaptans in 50–94% yields via NaIO 4 oxidation of the intermediate hydrobenzoquinones. Subsequent addition of primary and secondary amines, in the presence of air as an oxidizing agent, gave a range of 2-thio-5-amino-substituted benzoquinones. No oxidation at sulfur was detected under the described conditions.; Chapter 5. Various 2-alkylthio-5-amino- and 2,5-bis-amino-1,4-benzoquinone diimines were prepared by treatment of N-(1,3-dimethylbutyl)-N ′-phenyl-1,4-phenylene-diamine with thiols and amines using air as an oxidizing agent. Key 2-alkylthio-1,4-benzoquinone diimines were prepared via Ag2O oxidation of the corresponding 1,4-phenylene diamines.; Chapter 6. A new synthetic approach towards the synthesis of 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones and 2H-1,4-benzothiazin-3(4H)-ones is presented in this paper. Nucleophilic additions of α- and β-mercaptoalkanoate esters and acids to benzoquinone diimines, followed by cyclization with trifluoroacetic acid or 1,3-dicyclohexylcarbodiimide (DCC), provide novel, high yielding syntheses of 2H-1,4-benzothiazin-3(4H)-ones and 2,3-dihydro-1,5-benzothiazepin-4(5 H)-ones, respectively. |
