Microwave-assisted coupling reaction of N-aryl sydnones with 2-nitromethylenethiazolidine: unexpected formation of (Z)-2-(nitro((E)-p-substitutedphenyldiazenyl)methylene)thiazolidines.
TL;DR: The structures of all the new compounds were identified on the basis of the data obtained from the NMR, IR, X-ray diffraction spectra, HRMS measurements, and physical characteristics.
Abstract: Reaction of N-aryl sydnones with 2-nitromethylenethiazolidine straightforwardly gives rise to the formation of (Z)-2-(nitro((E)-p-substitutedphenyldiazenyl)methylene)thiazolidines in xylene and dimethoxyethane under microwave irradiation. A meaningful and plausible mechanism for this transformation is proposed, which anticipates the extrusion of an aceto-lactone-like moiety before a coupling occurs. The structures of all the new compounds were identified on the basis of the data obtained from the NMR, IR, X-ray diffraction spectra, HRMS measurements, and physical characteristics.
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TL;DR: This review provides comprehensive knowledge on the chemistry of ketene N,S-acetals, which make them versatile and easy to use, especially in cyclization and multicomponent reactions for the synthesis of various heterocyclic systems and related natural products.
Abstract: Push–pull alkenes, which bear electron-donating and -accepting group(s) at both termini of a C═C double bond, respectively, are of interest not only for their unique electronic properties but also for their importance as versatile building blocks in organic synthesis. In the world of ketene acetals having the push–pull alkene skeleton, ketene N,S-acetal is most likely the biggest family according to the number and types of these compounds. The first ketene N,S-acetal compound was reported in 1956. As a cyclic ketene N,S-acetal compound, nithiazine, the first lead structure of neonicotinoid insecticides, was reported in 1978. The characteristics of ketene N,S-acetals, which have the structural feature of ketene S,S-acetals and enaminones, make them versatile and easy to use, especially in cyclization and multicomponent reactions for the synthesis of various heterocyclic systems and related natural products. There has been an increasing wealth of information about the synthesis and synthetic applications of...
115 citations
TL;DR: A novel synthetic methodology was developed for the N-arylation of nitroenamine derivatives utilizing diaryliodonium triflates and copper(I) chloride as a catalyst to enable the easy aryl transfer from the hypervalent species under mild catalytic conditions with unusual heteroatom preference and high efficiency.
Abstract: A novel synthetic methodology was developed for the N-arylation of nitroenamine derivatives utilizing diaryliodonium triflates and copper(I) chloride as a catalyst. The procedure enables the easy aryl transfer from the hypervalent species under mild catalytic conditions with unusual heteroatom preference and high efficiency.
12 citations
TL;DR: In this article, a 2,2,2-trifluoroethanol-activated one-pot reaction of β-nitroenamines, secondary amines and aromatic aldehydes was developed under mild and convenient conditions.
12 citations
TL;DR: The reaction of C-(4-substituted-phenyl)-N-(benzoyl)-N-methylglycines with benzo[b]thiophene 1,1-dioxide unexpectedly gave benzothiophene-fused pyrrole derivatives in toluene under microwave irradiation via a cycloaddition and metal-free Pummerer-type sulfone deoxygenation path.
Abstract: The reaction of C-(4-substituted-phenyl)-N-(benzoyl)-N-methylglycines with benzo[b]thiophene 1,1-dioxide unexpectedly gave benzothiophene-fused pyrrole derivatives in toluene under microwave irradiation via a cycloaddition and metal-free Pummerer-type sulfone deoxygenation path. In order to obtain the desired sulfone derivatives, the sulfide group underwent oxidation with m-CPBA to afford sulfones. The structures of all the new products were elucidated by spectroscopic/physical methods and, in two cases, by X-ray diffraction.
8 citations
TL;DR: In this article, a series of methyl oxopyrazolidinium ylides was reacted with (E)-3-(2-hydroxyphenyl)-2-(phenylsulfonyl) acrylonitrile and 2-phenyl sulfonitrile to give rise to (1R,2S,3S)-5-methyl-7-oxo-1,3-p-substituteddiphenyl-2-(PSA)-hexahydropyrazolo[1,2-a]pyrazole
6 citations
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TL;DR: In this paper, the predicted properties and synthesis of sydnones are discussed. But they do not discuss the properties and properties of the sydnone at the C4 position.
156 citations
125 citations
TL;DR: High level ab initio calculations have been applied to the estimation of ring strain energies (SE) of a series of three- and six-member ring compounds, and marked increases in the SE of silacyclopropane and siladioxirane have been established, while significant decreases in theSEs of phosphorus, sulfur, dioxa- and diaza-containing three-member rings were observed.
Abstract: High level ab initio calculations have been applied to the estimation of ring strain energies (SE) of a series of three- and six-member ring compounds. The SE of cyclohexane has been estimated to be 2.2 kcal/mol at the CBS-APNO level of theory. The SE of cyclopropane has been increased to 28.6 kcal/mol after correction for the one-half of the SE of cyclohexane. The SEs of a series of carbonyl-containing three-member ring compounds have been estimated at the CBS-Q level by their combination with cyclopropane to produce a six-member ring reference compound. The SEs of cyclopropanone (5), the simplest α-lactone (6) [oxiranone], and α-lactam (7) [aziridinone] have been predicted to be 49, 47, and 55 kcal/mol, respectively, after correction for the SE of the corresponding six-member ring reference compound. The SEs of cyclohexanone, δ-valerolactone, and δ-valerolactam have been estimated to be 4.3, 11.3, and 5.1 kcal/mol, respectively. Marked increases in the SE of silacyclopropane and siladioxirane have been ...
98 citations
TL;DR: A new lead structure, 15, was identified to have improved anti-proliferative activities in U 937 cells, to induce apoptosis in U937, M12 and DU145 cancer cells, and to arrest U9 37 cells at the S-phase.
72 citations
TL;DR: The in vitro anti-protozoal and cytotoxic activities of these novel heterocyclic compounds were investigated.
53 citations