1027179-17-4

Basic information

• Product Name: toluene-4-sulfonic acid 2-(3-phenyl-prop-2-ynylamino)-phenyl ester
• Synonyms: toluene-4-sulfonic acid 2-(3-phenyl-prop-2-ynylamino)-phenyl ester
• CAS NO: 1027179-17-4
• Molecular Weight: 377.464
• Mol File: 1027179-17-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: toluene-4-sulfonic acid 2-(3-phenyl-prop-2-ynylamino)-phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: toluene-4-sulfonic acid 2-(3-phenyl-prop-2-ynylamino)-phenyl ester(1027179-17-4)
• EPA Substance Registry System: toluene-4-sulfonic acid 2-(3-phenyl-prop-2-ynylamino)-phenyl ester(1027179-17-4)

Safety Data

• Hazardous Substances Data: 1027179-17-4(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 326598-28-1 2-(N-prop-2'-ynylamino)phenyl p-toluenesulfonate 
• 98-59-9 p-toluenesulfonyl chloride 
• 95-55-6 2-amino-phenol 
• 1216-96-2 2-aminophenyl p-toluenesulfonate 

Downstream Products

• 326598-40-7 2-(3-phenyl-prop-2-ynylamino)-phenol 

Relevant articles and documents

Palladium-catalyzed heteroannulation leading to heterocyclic structures with two heteroatoms: A highly regio- and stereoselective synthesis of (Z)-4-alkyl-2-alkyl(aryl)idene-3,4-dihydro-2H-1,4,-benzoxazines and (Z)-3-alkyl(aryl)idene-4-tosyl-3,4-dihydro-2H-1,4-benzoxazines

A highly convenient method has been developed for the synthesis of (Z)-4-alkyl-2-alkyl(aryl)idene-3,4-dihydro-2H-1,4-benzoxazines 9 and (Z)-3-alkyl(aryl)idene-4-tosyl-3,4-dihydro-2H-1,4-benzoxazines 34-38 through palladium - copper-catalyzed reactions. Aryl halides 7 reacted with 2-[Nalkyl(benzyl)-N-prop-2′-ynyl]aminophenyl tosylate 6 in the presence of (PPh3)2PdCl2 (3 mol %), CuI(5 mol %) in triethylamine at room temperature to yield 2-[N-alkyl(benzyl)-N-(3-aryl-prop-2′-ynyl)]aminophenyl tosylates 8 in extremely good yields (72-96%). The latter could then be cyclized with KOH in ethanol - water to Z-9 in a highly regio- and stereoselective manner. Similarly, palladium copper-catalyzed reaction of 2-(prop-2′-ynyloxy)aniline (21) with aryl iodides 7 led to 22-26 which after tosylation and cyclization with cuprous iodide in CH3CN in the presence of K2CO3 and Bu4-NBr led to the (Z)-3-alkyl(aryl)idene-4-tosyl 3,4-dihydro-2H-1,4-benzoxazines 34-38 in good overall yields. The Z-stereochemistry of the products was established from 1H NMR spectra, 3JCH values (between vinylic proton and methylenic carbon of the heterocyclic ring), NOE experiments, and X-ray analysis· The method was also found to be suitable for the synthesis of bis(benzoxazinylated) derivatives 17, 39, and 2-alkyl-3,4-dihydro-2H-1,4-benzoxazines 18. Our method for the synthesis of 3,4-dihydro-2H-1,4-benzoxazines is highly efficacious, using easily available starting materials under very mild conditions. Also the synthesis of some novel 5-substituted uracil derivatives 40 and 41 containing the benzoxazinyl moiety and of potential biological interest is being reported.