113261-09-9

Upstream product

• 10283-95-1 N-allylbenzamide 
• 882-33-7 diphenyldisulfane 
• 98-88-4 benzoyl chloride 
• 14204-24-1 N-(phenylthio)succinimide 
• 80-17-1 benzenesufonyl hydrazide 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Boron-catalyzed arylthiooxygenation of n -allylamides: Synthesis of (arylsulfanyl)oxazolines

Oxazoles and aryl sulfides are chemical entities that are found in many natural products and biologically and pharmaceutically active molecules. It is therefore highly desirable to develop an efficient and practical approach to the synthesis of arylsulfanyl-substituted oxazolines. We developed a simple and efficient method for boron-catalyzed sequential arylsulfanylation and oxygenation of N-allylamides. The protocol uses readily available 1-(arylsulfanyl)pyrrolidine-2,5-diones as the arylsulfanylation reagents and inexpensive boron trifluoride etherate as the catalyst; no ligands or additives are required, and it is not necessary to purge the reaction vessel of air. The method therefore provides an efficient and practical strategy for the synthesis of arylsulfanyl-substituted heterocycles.

Electrochemical Chalcogenation of β,γ-Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines

The current report represents a transition-metal-free synthesis of oxazoline and isoxazoline derivatives by a tandem electro-oxidative chalcogenation-cyclization process. Both C?Se and C?S bond-forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline derivatives were synthesized with up to 91% isolated yield. (Figure presented.).

Improved Synthetic Method for 5-[(Phenylthio)methyl]oxazoline Derivatives: Electrophilic Cyclization of Allylic Amide Using a Bronsted Acid and Tetrabutylammonium Chloride under Mild Conditions

The synthesis of oxazolines using electrophilic cyclization of allylic amide is a simple and powerful method. However, cyclization involving arylsulfenylation requires harsh reaction conditions. We found that the reaction proceeds under mild heating conditions with the combination of a Bronsted acid and tetrabutylammonium chloride. This method enabled the synthesis of 5-[(arylsulfenyl)methyl]oxazoline derivatives under mild conditions and demonstrated high tolerance for various functional groups.

Iodine-promoted cyclization of N-propynyl amides and N-allyl amides via sulfonylation and sulfenylation

An iodine-promoted regioselective cyclization of N-propynyl/allyl amides with sulfonyl hydrazides has been developed for the synthesis of 5-methyl-arylsulfonyloxazoles and 5-methyl-arylthiooxazolines via sulfonylation and sulfenylation reactions. The notable features of this reaction are the formation of new C-S and C-O bonds, the broad functional group tolerance, and its applicability to alkyl sulfonyl hydrazides as well as internal alkynes.

New Routes to Heterocycles via Sulphenylation of Unsaturated Amides

The reaction of manganese(III) acetate with diphenyl disulphide in dichloromethane-trifluoroacetic acid in the presence of N-allylacetamide, followed by hydrolysis, affords a vicinal hydroxy sulphide.Similarly, addition to N-allyltrifluoroacetamide affords hydroxy sulphide adducts, but with different regioselectivity.N-Allylbenzamide and other unsaturated benzamides under similar conditions give cyclic products, 4,5-dihydro-1,3-oxazoles.Homoallylic amides give 5,6-dihydro-4H-1,3-oxazines.Amides derived from pent-4-enylamine give substituted pyrrolidines by cyclisation through nitrogen, but N-hex-5-enylbenzamide gives only an acyclic adduct.Unsaturated carboxylic acids and unsaturated carboxamides are transformed in good yield into lactones under similar conditions.

NEW ROUTES TO HETEROCYCLES VIA SULPHENYLATION OF UNSATURATED AMIDES

Reaction of manganic acetate with organic disulphides in dichloromethane trifluoroacetic acid in the presence of a variety of unsaturated amides leads to intramolecular cyclisation with formation of sulphenylated oxazolines, oxazines or tetrahydropyrroles.