17900-53-7

Upstream product

• 2031-13-2 3-methyl-2-(toluene-4-sulfonyl)-3,6-dihydro-2H-[1,2]thiazine 1-oxide 
• 491879-61-9 4-methyl-N-(1-methylprop-2-ynyl)-benzenesulfonamide 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 78-94-4 methyl vinyl ketone 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 2004-70-8 1-methylbuta-1,3-diene 
• 78388-18-8 N-(1-methyl-allyl)-4-methyl-benzenesulfonamide 
• 832-41-7 N-(ethoxymethyl)-4-methylbenzenesulfonamide 
• 142363-45-9 1-propynyl(phenyl)iodonium triflate 
• 144422-87-7 (E)-N-(2-hydroxypent-3-en-1-yl)-4-methylbenzenesulfonamide 

Downstream Products

• 132725-39-4 N-(4-methylbenzenesulfonyl)-4-methyl-1-amino-naphthalene 

Relevant academic research and scientific papers

Copper-catalyzed domino homologation and cycloisomerization reactions for 3-pyrroline synthesis

Copper bromide was found to be an efficient catalyst for a domino reaction sequence leading to 3-pyrrolines. The Cu(I)-catalyzed Crabbe reaction of propargyl sulfonamide and selective cycloisomerization of the allene intermediate were carried out using microwave irradiation conditions affording a wide range of 2-substituted- and 2,5-disubstituted-3-pyrrolines. Mechanistic studies of the reaction intermediates revealed two possible reaction pathways; both invoke the importance of vinyl copper intermediates.

Cross metathesis of N-allylamines and α,β-unsaturated carbonyl compounds: A one-pot synthesis of substituted pyrroles

A tandem reaction involving cross metathesis followed by concomitant cyclisation has been developed for the synthesis of substituted pyrroles. Various protected electron-deficient N-allylamines reacted with α,β-unsaturated carbonyl compounds in the presen

A metathesis approach to aromatic heterocycles

The ring closing metathesis (RCM) reaction can be used to prepare substituted furans and pyrroles. By utilising a Pd-catalysed coupling reaction with methoxyallene, allylic alcohols and sulfonamides can be converted into substrates that are ideal precursors to ring closing metathesis. After the RCM reaction is complete, the addition of acid promotes an elimination of methanol to form the fully aromatised system. A range of different substitution patterns and functional groups are compatible with this sequence. Double allene coupling, RCM and elimination reactions are also possible and allow the formation of biaryl systems. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Inter- and intramolecular addition/cyclizations of sulfonamide anions with alkynyliodonium triflates. Synthesis of dihydropyrrole, pyrrole, indole, and tosylenamide heterocycles

The synthesis of dihydropyrroles, pyrroles, and indoles through [3-atom + 2-atom] combination of ethyl or aryl tosylamide anions with phenyl(propynyl)iodonium triflate, and the base-mediated intramolecular bicyclization of alkynyliodonium-bearing tosylamide or tosylimide substrates to furnish bicyclic and tricyclic tosylenamide (-enimide) products, is described. A detailed discussion of the scope, limitations, byproduct formation, and the basis for observed diastereoselectivity is presented.

N-p-Toluenesulfonylpyrroles from 1,3-dienes

1,3-Dienes can be converted to N-p-toluenesulfonylpyrroles in two steps: 1) [4+2]-cycloaddition with N-sulfinyl-p-toluenesulfonamide and 2) conversion of the 3,6-dihydro-1,2-thiazine oxide adduct to a pyrrole using triethylamine-trimethylphosphite.

Palladium(II) Catalysed 5-endo-trigonal Cyclization of 2-Hydroxybut-3-enylamines: Synthesis of Five-membered Nitrogen Heterocycles

2-Hydroxybut-3-enylamines 1 undergo a novel PdII-catalysed 5-endo-trigonal cyclization to provide pyrrolines 2, pyrroles 3, and/or 3-oxopyrrolidines 4 in good to moderate combined isolated yields; the hydroxy group is essential for the cyclizat