A one-pot, non-catalytic approach to 1,2,4-benzothiadiazine-1,1-dioxides

Cherepakha, Artem; Kovtunenko, Vladimir O.; Tolmachev, Andrey A.; Lukin, Oleg

doi:10.1016/j.tet.2011.06.063

Cited by 19 publications

(6 citation statements)

References 14 publications

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“…The presence of electron‐deficient groups on the phenyl ring of ortho ‐halo‐arylsulfonyl chloride 204 is reported to be necessary for success of the one‐pot non‐catalytic procedure (scheme 68, condition A). Bromine‐substituted benzenesulfonyl chloride 204 converted to desired compound 209 via Ullmann method with CuI as the catalyst and DMEDA as the ligand (Scheme 68, condition B) [132] …”

Section: Recent Ullman‐goldberg And/or Buchwald‐hartwig Reports In Li...mentioning

confidence: 99%

Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

et al. 2021

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The Carbon-Nitrogen bond formation has always been an important and useful tool in drug discovery. Its wide applications in synthesizing N-heterocycles, known as the most prevalent moiety in the active pharmacophores, have attracted increasing attention from researchers. In recent years many works were devoted to finding new and more rapid and effective chemo-and regio-selective methods for the synthesis of N-containing heterocycles. Buchwald-Hartwig and Ullman-Goldberg are two proven efficient methods for synthesizing five, six, and seven-membered heterocycles found abundantly in literature. Here, we study these two amination methods more precisely, based on the reaction conditions and the products.

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Section: Recent Ullman‐goldberg And/or Buchwald‐hartwig Reports In Li...mentioning

confidence: 99%

Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

et al. 2021

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“…Synthesis via the reaction of 2-aminosulfonamides with aldehydes is another method that has been used [ 16 ]. Other authors have reported the reaction of 2-halobenzenesulfonyl chlorides with amidines and aminopyridines in the presence of potassium carbonate [ 17 ]. The synthetic method in which substituted amidines react with TosNSO ( N -sulfinyl- p -toluenesulfonamide) in acetic acid and hydrogen peroxide has also been described [ 18 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological activity of novel 3-heteroaryl-2H-pyrido[4,3-e][1,2,4]thiadiazine and 3-heteroaryl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxides

et al. 2013

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A series of novel 1,2,4-thiadiazine 1,1-dioxides were synthesized by condensation of 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide with heterocyclic methyl carbimidates obtained from heterocyclic carbonitriles and used at the time of their creation. Substituted amidines were isolated as the intermediates in the reaction with 2-chlorobenzenesulfonamide. Those intermediates were successfully cyclized to corresponding 1,2,4-thiadiazine 1,1-dioxides in pyridine with the addition of DBU. The newly synthesized compounds were evaluated for their tuberculostatic and anticancer activities. Eight compounds were able to inhibit the growth of some renal and non-small cell lung cancer cell lines.Graphical Abstract

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“…A number of benzothiadiazine 1,1-dioxide derivatives have recently been reported to display numerous biological activities [16][17][18][19][20][21][22]. A literature search reveals © Kumar P.P.S., Suchetan P.A., Sreenivasa S., Naveen S., Lokanath N.K., Kumar D.B.A., 2015 that 1,2,4-benzothiadiazine 1,1-dioxides are generally synthesized either by condensation of o-amino benzene sulfonamides with urea at elevated temperatures [ 23 ] or by the reaction of o-amino benzene sulfonamide with isocyanates in DMF under reflux [ 24 ]. Although various approaches to the preparation of 1,2,4-benzothiadiazine 1,1dioxide derivatives have been reported [25][26][27][28][29][30][31], the development of a simpler method for the synthesis of the 1,2,4benzothiadiazine 1,1-dioxide moiety is still desirable because of their biological significance.…”

Section: Introductionmentioning

confidence: 99%

Molecular and Crystal Structures of Two 1,2,4-Benzothiadiazine Derivatives

2015

JSC

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The synthesis of two 1,2,4-benzothiadiazine derivatives, namely, 6-bromo-4H-spiro[1,2,4-benzothiadiazine-3,1c-cyclobutane] 1,1-dioxide (1) and 6-bromo-1c-ethyl-4H-spiro[1,2,4-benzothiadiazine-3,4c-piperidine] 1,1-dioxide (2) is described in the present work. The synthesized compounds were studied by IR, 1 H and 13 C NMR, and single crystal X-ray diffraction to determine their molecular and crystal structure. In both structures the conformation of the 1,2,4thiadiazinane ring is a twisted chair and is stabilized by the intramolecular interaction of the C-H…O type. Compound 1 crystallizes in the monoclinic crystal system and space group C2/c with the unit cell parameters a = 15.8690(17) Å, b = 12.1453(16) Å, c = 12.0152(15) Å, E = 99.686(7)q, Z = 8 and V = 2282.7(5) Å 3. Compound 2 crystallizes in the monoclinic crystal system and space group P 2 1 /c with the unit cell parameters a = 14.5748(6) Å, b = 9.3340(5) Å, c = 12.4283(6) Å, E = 112.757(2)q, Z = 4 and V = 1559.14(13) Å 3. In the crystal structures different packing motifs are implemented with the formation of supramolecular assemblies of different types due to classical hydrogen bonds such as N-H…O and intermolecular interactions of N-H…Br, N-H…N, C-H…O types and S…S stacking.

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A one-pot, non-catalytic approach to 1,2,4-benzothiadiazine-1,1-dioxides

Cited by 19 publications

References 14 publications

Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

Ullmann‐Goldberg and Buchwald‐Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N‐Heterocycles

Synthesis and biological activity of novel 3-heteroaryl-2H-pyrido[4,3-e][1,2,4]thiadiazine and 3-heteroaryl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxides

Molecular and Crystal Structures of Two 1,2,4-Benzothiadiazine Derivatives

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