69640-27-3

Upstream product

• 95482-65-8 4-(dimethylamino)-5,6-bis(methoxycarbonyl)-2-phenyl-4H-1,3-thiazine 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 202286-41-7 N-(benzotriazol-1-ylmethyl)-α-(methylthio)phenylimine 
• 111680-71-8 2-(dimethylamino)-4-oxo-4H-pyrido<1,2-a>pyrimidine-3-carbaldehyde 
• 922-67-8 propynoic acid methyl ester 
• 24461-61-8 phenylglycine methyl ester 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 591-51-5 phenyllithium 
• 39533-32-9 methyl 2-isocyano-2-phenylacetate 
• 106762-16-7 phenyl<<(trimethylsilyl)methyl>amino>acetonitrile 
• 100-52-7 benzaldehyde 
• 117067-55-7 N-(benzotriazol-1-ylmethyl)thiobenzoamide 
• 101402-19-1 N-Phenyl-N'-trimethylsilanylmethyl-benzamidine 
• 101402-19-1 N-Phenyl-N'-trimethylsilanylmethyl-benzamidine 

Relevant academic research and scientific papers

Regioselective Synthesis of Pyrroles from Alkyne-Isocyanide Click Reactions: An Angle Strain-Induced Bond Migration Approach

The direct regioselective synthesis of highly functionalized pyrroles with two different electron-withdrawing groups has been developed using an angle strain-induced 1,2-shift of an electron-withdrawing group in 2H-pyrroles. The preferential migration aptitude of an electron-withdrawing group over alkyl and aryl groups is believed to be the result of the orbital overlap between the internal alkene and the electron-withdrawing group. The newly developed regioselective synthesis of pyrroles features a wide substrate scope, simple reaction set-up, and high yields (60–82%), capturing the essence of alkyne-isocyanide “click” reactions. (Figure presented.).

Reaction of functionalized azomethine ylides with acetylenic dipolarophiles: the facile synthesis of functionalized 2H- and 1H-pyrroles

The reaction of functionalized azomethine ylides as C-unsubstituted nitrile ylide equivalents with acetylenic dipolarophiles is mentioned. Therein, the initially formed cycloadducts, 2,5-dihydropyrroles, by the reaction of the azomethine ylides with subst

Unprecedented 1,4-stannatropy: Effective generation of azomethine ylides as nitrile ylide equivalents from N-(stannylmethyl)thioamides

Generation and cycloaddition of less- or non-stabilized azomethine ylides, or nitrile ylide equivalents, via unprecedented 1,4-stannatropy of N-(tributylstannylmethyl)thioamides were achieved. The reactions with dipolarophiles, such as electron-deficient alkenes and alkynes, afforded corresponding pyrrolidine and pyrrole derivatives effectively. The Royal Society of Chemistry 2006.

Novel generation and cycloaddition of N-silylated azomethine ylides from α-silylimidates and trifluorosilane

The Generation of N-silylated azomethine ylides was achieved by the reaction of α-silylimidates and trifluorophenylsilane. The generated azomethine ylides can be regarded as synthetic equivalents of nitrile ylides since they have an alkoxy group which may

Novel and convenient routes to substituted pyrroles and imidazoles

S-Methyl N-(benzotriazol-1-ylmethyl)thioimidate 6 is obtained by lithiation of the corresponding N-(benzotriazol-1-ylmethyl)thioamide 5 and subsequent reaction with methyl iodide. Derivative 6 undergoes [2+3] cycloaddition reactions with α,β-unsaturated -esters, -ketones and -nitriles, and vinylpyridines which are followed by elimination of benzotriazole and the thioalkoxy group, to give 2,3,4-trisubstituted pyrroles. Lithiation of 6 followed by reactions with imines gives cyclized 4,5-dihydroimidazoles 14 which upon further treatment with ZnBr2 or direct refluxing in toluene yield the 1,2,5-trisubstituted imidazoles 15 in good yields.

Reduction electrochimique de 4H-1,3-thiazines : obtention de 6H-1,3-thiazines et (ou) de pyrroles substitues

Controlled potential electroreduction (protic medium, mercury cathode) of substituted 2-ethoxy and 2-phenyl-4H-1,3-thiazines leads to 6H-1,3-thiazines and (or) pyrroles.The nature of the isolated products appears strongly dependent on pH of the medium and

A selective electrochemical way to functionalized 6H-1,3-thiazines and/or pyrroles

4H-1,3-thiazines, easily prepared from 1-thia-3-azabutadienes, appear electroactive in protic medium. Controlled potential electroreductions of 4H-1,3-thiazines lead either to substituted 6H-1,3-thiazines or to pyrroles according to the nature of the C-4

Silyl-Substituted Thioimidates as Nitrile Ylide Equivalents

Treatment of silyl-substituted thioimidates with silver fluoride in the presence of a trapping agent produces dipolar cycloadducts formally derived from nitrile ylides.The ratio of cycloadducts obtained from the reaction of unsymmetrically substituted dip

A New and General Route to N-Protonated Azomethine Ylides from N-(Silylmethyl)amidines and -thioamides. Cycloaddition of Synthetic Equivalents of Nitrile Ylides

The N- or S-alkylation or -silylation of N-(silylmethyl)amidines or -thioamides and the subsequent desilylation of the silylmethyl group generate N-protonated azomethine ylides bearing a leaving group.These azomethine ylides undergo successful cycloaddition with electron-deficient olefins, acetylenes, and aldehydes.As the leaving group is eliminated under the reaction conditions, these azomethine ylides can be synthetic equivalents of nonstabilized nitrile ylides which are otherwise relatively inaccessible.

N-PROTONATED AZOMETHINE YLIDES WITH A LEAVING GROUP AS SYNTHETIC EQUIVALENTS FOR NONSTABILIZED NITRILE YLIDES

Through alkylation or silylation and then desilylation steps, N-(silylmethyl)amidines generate N-protonated azomethine ylides which cycloadd to olefins, acetylenes, and aldehydes giving 1- or 2-pyrrolines, pyrroles, and 2-oxazolines, respectively, after the elimination of N-substituted anilines.With this sequence, the amidines are useful synthetic equivalents of nonstabilized nitrile ylides.