21399-31-5

Upstream product

• 103896-55-5 N-(1-Phenylvinylimino)triphenylphosphorane 
• 619-41-0 4-(bromoacetyl)toluene 
• 5044-52-0 vinyltriphenylphosphonium bromide 
• 208463-69-8 2-Phenyl-4-p-tolyl-oxazol-5-ol 
• 1132645-43-2 4-(4-methylphenyl)-1-phenylbut-3-yn-1-yl azide 
• 1350307-59-3 2-aceto-1-(4-methylphenyl)-4-phenylbutane-1,4-dione 
• 40794-87-4 1-(4-methylphenyl)-4-phenyl-1,4-butanedione 
• 70-11-1 α-bromoacetophenone 
• 378186-93-7 1-(4-methylphenyl)-2,3-butadien-1-one 
• 60295-09-2 4'-methylacetophenone carbo-t-butoxyhydrazone 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 122-00-9 para-methylacetophenone 
• 16717-64-9 1-azidostyrene 
• 766-97-2 4-n-methylphenylacetylene 

Relevant academic research and scientific papers

Switchable reactivity between vinyl azides and terminal alkyne by nano copper catalysis

A novel nano copper-catalyzed substrate-dependent chemodivergent transformation of vinyl azides with a terminal alkyne is disclosed. 2,5-Disubstituted pyrroles were selectively obtained in high yield with aryl alkynes and aliphatic alkynes, whereas 2,3,4-trisubstituted pyrroles were formed with silylated alkynes. This switchable method provides a controllable and facile access to both multisubstituted pyrrole scaffolds with high efficiency, excellent regioselectivity, and good functional group compatibility.

Rhodium-Catalyzed Oxidative Cycloaddition of N-tert-Butoxycarbonylhydrazones with Alkynes for the Synthesis of Functionalized Pyrroles via C(sp3)–H Bond Functionalization

A rhodium(III)-catalyzed cycloaddition of N-tert-butoxycarbonylhydrazones with internal alkynes was developed. The reaction features a regioselective α-imino alkyl C(sp3)?H bond functionalization resulting in selective formation of highly functionalized NH-free pyrroles. Our studies showed that utilizing the N-tert-butoxycarbonyl (N-Boc) as the oxidizing directing group is critical for achieving the observed pyrrole formation versus the isoquinoline formation. To account for the pyrrole formation, we hypothesized that a prior tautomerization of the N-Boc-hydrazones to enamines should occur, followed by regioselective C(sp2)–H cleavage to form a putative five-membered rhodacycle. Subsequent coupling of the rhodacycle with the alkynes would afford the pyrrole products. (Figure presented.).

Tandem reaction of 1,2-allenic ketone with α-halo ketone or α-halo ester in water: An efficient and sustainable synthesis of 1,3,4′-tricarbonyl compounds

An efficient and sustainable synthesis of the otherwise difficult to obtain 1,3,4′-tricarbonyl compounds through a water mediated, TBAF·3H2O promoted unprecedented tandem reaction of 1,2-allenic ketone with α-halo ketone or α-halo ester has been developed. Remarkably enhanced reactivity and improved chemoselectivity by using water as the reaction medium was observed. The 1,3,4′-tricarbonyl compounds facilitate further versatile transformations, which underscores the importance of these products as synthetic intermediates. The Royal Society of Chemistry.

Microwave-assisted zinc chloride-catalyzed synthesis of substituted pyrroles from homopropargyl azides

Ligand-free 5-endo-dig cyclization of 1,4- and 1,2,4-substituted but-3-yn-1-yl (homopropargyl) azides in the presence of zinc chloride (usually 20 mol %) in dichloroethane at elevated temperature provides 2,5-di- and 2,3,5-trisubstituted pyrroles in high

5(4H)-oxazolones. Part XI. Cycloaddition reaction of oxazolones and munchnones to triphenylvinylphosphonium salts as synthetic equivalents of alkynes

5(4H)-Oxazolones 1 and milnchnones 3 are reacted with triphenylvinylphosphonium bromide 2a to give, through a cycloaddition reaction, pyrrole derivatives 4a-d and 7a-c unsubstituted at C-3 and C-4. The use of substituted vinylphosphonium salts 2b,c and dipoles 1 and 3 allows the isolation of 3-methylpyrroles 4e, f and 7d,e and 3-pyrrolecarboxylic acids 9a-c, respectively. The cycloaddition reactions proceed with high regionelectivity because of the positive interaction of phosphonium group of 2 and carbonyl group of dipoles 1 and 3.

ON THE REACTION OF N-VINYLIMINOPHOSPHORANES 3. A NOVEL ROUTE TO PHENYL-SUBSTITUTED PYRROLES BY THE REACTION OF N-(1-PHENYLVINYL)-IMINOPHOSPHORANES WITH α-BROMO KETONES

N-(1-phenylvinyl)iminotriphenylphosphorane or N-(1-phenyl-vinyl)iminotributylphosphorane reacted with α-bromo ketones to give phenyl-substituted pyrroles via a novel C-C bond formation followed by aza-Wittig reaction.