A mild and efficient synthesis of 3-Aminosubstituted Isothiazole S-Oxides and their 5-Sulfanylsubstituted derivatives (original) (raw)
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ChemInform, 2009
A mild and efficient method for the synthesis of diverse isoindolinones from o-phthaldehydic acid methylthiomethyl ester and aliphatic/aromatic amines has been developed. A number of nucleophiles including a hydride ion were successfully added to the intermediate Schiff's base providing isoindolinones, with or without substitution at 3-position. Conditions have also been developed for amines with an integrated nucleophilic group to react in a diverse fashion either to give isoindolinones or tricyclic g-lactams as single diastereoisomers in very good yield.
European Journal of Medicinal Chemistry, 2006
5-Sulfanyl-3-alkylaminoisothiazole dioxide derivatives have been identified as a new class of potent inhibitors of rat aortic myocite proliferation. They were prepared by applying a simple methodology able to introduce a heteroatom on C-5 of the 3-alkylaminoisothiazole dioxide system. 3-Aminosubstituted-5-chloroisothiazole dioxides react smoothly not only with S-nucleophiles but also with N-and O-nucleophiles affording the corresponding 5-heterosubstituted isothiazole dioxides through an addition-elimination reaction. The behavior of 3-alkylamino-4bromo-isothiazole 1,1-dioxide with S-, N-and O-nucleophiles affording the same products has also been described. On the contrary, the 3amino-4,5-unsubstituted isothiazole dioxide system reacts easily only with sulfur nucleophiles affording the corresponding 4,5-dihydro-5-sulfanylderivatives through a simple Michael addition reaction.
Synthesis and Reactivity of Sulfamoyl Azides and 1-Sulfamoyl-1,2,3-triazoles
Organic Letters, 2011
Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of CuTC catalyst forming 1-sulfamoyl-1,2,3-triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins. Sulfamoyl azides make only a fleeting appearance in organic synthesis. Their first preparation from sulfamoyl chlorides and sodium azide was reported in 1956 by American Cyanamid chemists. 1 However, this generally reliable route fails when preparation of arylsulfamoyl azides is attempted due to the undesired chlorination of the aromatic ring by sulfuryl chloride. Shozda and Vernon, 2 and later Griffiths, 3 developed an alternative synthesis of arylsulfamoyl azides using chlorosulfonyl azide. While this method circumvented the problem of ring chlorination, the chlorosulfonyl azide reagent was highly explosive and difficult to handle. Furthermore, the yields were modest at best, remaining generally in the 15-50% range. Recently, imidazole-1-sulfonyl azide hydrochloride was shown to be an efficient and convenient diazo transfer reagent. 4 During our investigations, we found that alkylation of the imidazole nitrogen eliminated its diazo transfer reactivity and instead led to the transfer of the sulfonyl azide group. In this study, we introduce the imidazolium salt 2 as a novel and efficient sulfonyl azide transfer reagent. The 2-methylated derivative 1 was prepared using a slight modification of the method developed by Goddard-Borger and Sticks for the synthesis of imidazole-1-sulfonyl azide hydrochloride. 4 The added methyl group at C-2 of the imidazole ring improves solubility of this derivative in organic solvents 5 and is also expected to increase its stability. The free base of the imidazole 1 was efficiently alkylated with methyl triflate. The product was isolated as a crystalline solid, yielding the imidazolium sulfonyl azide transfer reagent 2 in
Efficient Synthesis of 1-Sulfonyl-1,2,3-triazoles
Organic Letters, 2010
An efficient room temperature method for the synthesis of 1-sulfonyl-1,2,3-triazoles from in situ generated copper(I) acetylides and sulfonyl azides is described. Copper(I) thiophene-2-carboxylate (CuTC) catalyst produces the title compounds under both non-basic anhydrous and aqueous conditions in good yields.
Helvetica Chimica Acta, 2009
The racemic N-benzylisothiazol-3-amine 1-oxide (2) was demonstrated to be an efficient partner in Diels -Alder reactions (Schemes 2 -4) and a good dipolarophile in 1,3-dipolar cycloaddition reactions with nitrile oxides (Scheme 5). Polycyclic isothiazole S-oxides with different substitution patterns were obtained from 2 in good yield and in a fully regioselective way. Improved diastereoselection was observed performing the Diels -Alder or 1,3-dipolar cycloaddition reactions in H 2 O.
Phosphorus, Sulfur, and Silicon and the Related Elements
A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a-5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1 H NMR, 13 C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs.
1-Substituted 5-Alkyl(aryl)sulfanyltetrazoles and Their Derivatives
Russian Journal of Organic Chemistry, 2000
The review analyzes published data on the synthesis, chemical properties, and application of 1-substituted 5-alkyl(aryl)sulfanyltetrazoles. Specific attention is given to reactions of metalated 1-alkyl(aryl)-5-alkylsulfonyltetrazoles with electrophilic reagents as a general and highly stereoselective method for the preparation of functionally substituted olefins.