58461-96-4

Upstream product

• 591-50-4 iodobenzene 
• 58432-15-8 3-(2-aminophenylthio)prop-1-yne 
• 4875-10-9 o-nitrothiophenol 
• 1794-48-5 1-bromo-3-phenylprop-2-yne 
• 137-07-5 2-amino-benzenethiol 
• 58432-13-6 3-(o-nitrophenylthio)-1-phenyl-1-propyne 

Downstream Products

• 95065-78-4 C₂₂H₁₆ClN₃O₂S 
• 95065-79-5 C₁₉H₁₇ClN₂O₂S 
• 260803-91-6 4-methyl-N-[2-(3-phenyl-prop-2-ynylsulfanyl)-phenyl]-benzenesulfonamide 
• 58432-21-6 3-phenyl-4H-benzo[b][1,2,3]triazolo[1,5-d][1,4]thiazine 
• 95065-85-3 2-(4-Nitro-phenyl)-3-phenyl-4H-5-thia-1,9b-diaza-cyclopenta[a]naphthalene 
• 95065-91-1 3-(4-Nitro-phenyl)-3-(1-phenyl-propa-1,2-dienyl)-3H-benzo[1,3,4]thiadiazine 
• 95083-53-7 3-Phenyl-4H-5-thia-1,9b-diaza-cyclopenta[a]naphthalene-2-carboxylic acid ethyl ester 
• 95065-89-7 3-(1-Phenyl-propa-1,2-dienyl)-3H-benzo[1,3,4]thiadiazine-3-carboxylic acid ethyl ester 
• 95065-84-2 2-ethoxycarbonyl-3-methylene-2a-phenyl-2a,3-dihydro<1,2>diazeto<4,1-c><1,4>benzothiazine 
• 59066-61-4 2-[(E)-styryl]benzothiazole 
• 260803-81-4 (E)-2-styryl-3-tosylbenzothiazoline 
• 58432-18-1 1-azido-2-(3-phenyl-prop-2-ynylsulfanyl)-benzene 

Relevant academic research and scientific papers

Palladium-copper catalyzed synthesis of benzofused heterocycles with two heteroatoms: Novel and highly regio- and stereoselective syntheses of (E)-2-(2-arylvinyl)-3-tosyl-2,3-dihydro-1,3-benzothiazoles and (E)-2-alkyl(aryl)idene-3,4-dihydro-2H-1,4-benzothiazines

A highly novel, general, and convenient palladium and copper-catalyzed procedure has been developed for the synthesis of (E)-2-(2-arylvinyl)-3-tosyl-2,3-dihydro-1,3-benzothiazoles 28-40. 3-(2-Aminophenylthio)prop-1-yne 1 reacts with aryl iodides 2-14 under palladium-copper catalysis to yield the disubstituted alkynes 15-27 which after tosylation undergo a novel cyclization with CuI in the presence of triethylamine in THF to (E)-2-(2-arylvinyl)-3-tosyl-2,3-dihydro-1,3-benzothiazoles 28-40 rather than to the expected 3-alkylidene-4-tosyl-3,4-dihydro-2H-1,4-benzothiazines 41. The reaction is highly regio- and stereoselective. The synthesis of 2-(2-arylethyl)-3-tosylbenzothiazolines 42-47, 2-(2-arylvinyl)benzothiazoles 48-54, and a novel 5-substituted uracil derivative 55 of potential biological importance is also being reported. Similarly,the palladium-copper-catalyzed arylation of S-[2-(N-prop-2′-ynyl)aminophenyl]-N,N-dimethylthiocarbamate 58 with aryl iodides yields the disubstituted alkynes 59 which on cyclization with KOH in methanol leads to (E)-2-(2-aryl)methylidene-3,4-dihydro-2H-1,4-benzothiazines 61. The reaction of the diiodo compounds 12-14a, however, with 58 under palladium-copper-catalyzed reactions involves the participation of only one of the iodo groups in the heteroannulation process giving compounds 61i and 61j. These are amenable to further palladium-catalyzed reactions and afford polyunsaturated heteroaromatic compounds 62 and 63.

Heteroannulation through copper catalysis: A novel cyclization leading to a highly regio- and stereoselective synthesis of 2-substituted benzothiazolines

(matrix presented) 3-(2-Aminophenylthio)prop-1-yne 8 reacted with aryl iodides 9-18 under palladium-copper catalysis leading to the disubstituted alkynes 19-28 which after tosylation underwent a novel cyclization under copper catalysis to 2-substituted be