15448-99-4Relevant articles and documents
New ring systems from 1,2-benzisothiazole-1,1-dioxides and related compounds
Abramovitch, Rudolph A.,Shinkai, Ichiro,Mavunkel,More,O'Connor, Sean,Ooi, Gino H.,Pennington, William T.,Srinivasan,Stowers, James R.
, p. 3339 - 3354 (1996)
Ring-expansions and ring-annulations based on 3-substituted 1,2-benzisothiazole-1,1-dioxides have lead to a variety of novel heterocyclic systems. The reaction of 3-substituted (1H)-1-isoindoles with 1-diethylamino-1-propyne has also resulted in new, ring-expanded molecules in good to modest yields.
Reaction of orthto-lithiated N-methylbenzamide with 1,2-Diketones: A novel highly efficient route to N-methylisoquinolin-1-one
Kiselyov, Alexander S.
, p. 493 - 496 (1995)
1,2-Diketones were found to react with ortho-lithlated N-methylbenzamide to give diols 4a-g in 59-80% yields. Reaction of diols 4a-g with the system Me3SiCl/Nal in MeCN furnished N-methylisoquinolin-1-ones in 84-92% yields.
Direct preparation of saccharin skeletons from N-methyl(o-methyl)arenesulfonamides with (diacetoxyiodo)arenes
Togo, Hideo,Katohgi, Masashi,Yokoyama, Masataka
, p. 131 - 132 (1998)
Various N-methylsaccharins were easily prepared in moderate to good yields by the reaction of N-methyl(o-methyl)arenesulfonamides with (diacetoxyiodo)arene in the presence of iodine under irradiation with a tungsten lamp. The present method is very useful for the direct preparation of saccharins with N-methyl(o-methyl)arenesulfonamides containing various substituents on the aromatic ring.
First observation of Chapman rearrangement of a pseudosaccharyl ether in the solid state: the thermal isomerization of 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide revisited
Almeida,Gómez-Zavaglia,Kaczor,Cristiano,Eusébio,Maria,Fausto
, p. 3296 - 3305 (2008)
3-(Methoxy)-1,2-benzisothiazole 1,1-dioxide, a pseudosaccharyl ether, was long ago known to undergo a thermal Chapman-like [1,3′]-isomerization to the corresponding N-methyl pseudosaccharin at temperatures above its melting point (ca. 184 °C) [Hettler H., Tetrahedron Lett. 1968, 15, 1793]. In the present study, it is shown that this rearrangement can also take place in the solid state, at temperatures as low as 150 °C. This was the first observation of a Chapman-like [1,3′]-isomerization in pseudosaccharyl ethers in the solid state. The study has been carried out by a multidisciplinary approach using temperature dependent infrared spectroscopy, differential scanning calorimetry (DSC), and polarized light thermomicroscopy, complemented by theoretical methods.
Bu4NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters
Ghosh, Subhendu,Mir, Bilal Ahmad,Patel, Bhisma K.,Rajamanickam, Suresh,Sah, Chitranjan,Sethi, Garima,Venkataramani, Sugumar,Yadav, Vinita
, p. 2118 - 2141 (2020/03/13)
Bu4NI-catalyzed regioselective N2-methylation, N2-Alkylation, and N2-Arylation of tetrazoles have been achieved using tert-butyl hydroperoxide (TBHP) as the methyl source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or arylating agents. Based on DFT calculations, it was found that spin density, transition-state barriers (kinetic control), and thermodynamic stability of the products (thermodynamic control) play essential roles in the observed regioselectivity during N-Alkylation. This radical-mediated process is amenable to a broad range of substrates and provides products in moderate to good yields.
Synthesis of (e)-n-substituted 1,2-benzothiazol-3(2h)-imine 1,1-dioxide derivatives from secondary benzenesulfonamides and isothiocyanates
Kobayashi, Kazuhiro,Fujiwara, Daiki
, p. 1275 - 1288 (2018/08/07)
A new and simple method for the preparation of (E)-N-substituted 1,2-benzothiazol-3(2H)-imine 1,1-dioxide derivatives has been developed. 2,N-Dilithiobenzenesulfonamides, generated by the treatment of secondary benzenesulfonamides with two equivalents of butyllithium, react with isothiocyanates to afford the corresponding 2-(aminosulfonyl)benzothioamides, which undergo ring closure with a formal elimination of hydrogen sulfide on treatment with thionyl chloride in the presence of two equivalents of pyridine to provide the desired products. Acid hydrolysis of some of these products leads to the formation of N-substituted saccharins.
