Iodine-mediated synthesis of 3-acylbenzothiadiazine 1,1-dioxides

Xi, Long‐Yi; Zhang, Ruoyi; Shi, Lei; Chen, Shanyong; Yu, Xiao‐Qi

doi:10.3762/bjoc.12.101

Cited by 4 publications

(3 citation statements)

References 35 publications

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“…The construction of the 3-acylbenzothiadiazine-1,1-dioxide skeleton through the reactiono fa ryl methyl ketones and 2aminobenzenesulfonamides has been reported( Scheme35). [47] Aryl methylk etones with EDGs or EWGs andh eteroaryl methyl ketones provide the products in moderate to good yields. Further,2 -aminobenzenesulfonamides with different substituents on the benzene ring have also been explored.…”

Section: Cànbond-forming Reactionsmentioning

confidence: 99%

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Metal‐Free Cross‐Dehydrogenative Coupling (CDC): Molecular Iodine as a Versatile Catalyst/Reagent for CDC Reactions

Parvatkar

Manetsch

Banik

2018

Chemistry An Asian Journal

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The development of ecofriendly methods for carbon-carbon (CÀC) and carbon-heteroatom (CÀHet) bond formation is of great significance in modern-dayr esearch. Metal-free cross-dehydrogenative coupling (CDC) has emerged as an important tool for organic and medicinal chemists as am eanst of orm CÀCa nd CÀHet bonds, as it is atom economical and more efficient and greenert han transition-metalc atalyzed CDC reactions. Molecular iodine (I 2 )i s recognized as an inexpensive, environmentally benign, and easy-to-handle catalyst or reagentt op ursueC DCs under mild reactionc onditions, with good regioselectivities and broad substrate compatibility.T his review presentst he recentd evelopmentso fI 2 -catalyzed CÀC, CÀN, CÀO, and CÀ S/CÀSe bond-forming reactions for the synthesis of various important organic molecules by cross-dehydrogenative coupling.Scheme1.Strategies for CÀCa nd CÀHet bond formation by CDC.[a] Dr. Scheme5.Synthesis of substituted indolizines.Scheme6.Synthesis of (E)-or (Z)-2-methylthio-1,4diones.Scheme7.Synthesis of indolo[2,3-b]carbazoles.Scheme8.Synthesis of p-amino phenyl diketones.Scheme9.Synthesis of functionalized cyclopropanes.Scheme10. Photooxidative coupling of thiophenesw ith carbonyls.Bz = benzoyl.Scheme65. Synthesis of 2-aminobenzothiazoles. PTSA = para-toluenesulfonic acid.Scheme66. Synthesis of b-decarbonylated sulfones.Scheme67. Synthesis of diheteroaryl thioethers.

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Section: Cànbond-forming Reactionsmentioning

confidence: 99%

“…The construction of the 3‐acylbenzothiadiazine‐1,1‐dioxide skeleton through the reaction of aryl methyl ketones and 2‐aminobenzenesulfonamides has been reported (Scheme ) . Aryl methyl ketones with EDGs or EWGs and heteroaryl methyl ketones provide the products in moderate to good yields.…”

Section: C−n Bond‐forming Reactionsmentioning

confidence: 99%

Metal‐Free Cross‐Dehydrogenative Coupling (CDC): Molecular Iodine as a Versatile Catalyst/Reagent for CDC Reactions

Parvatkar

Manetsch

Banik

2018

Chemistry An Asian Journal

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“…Literature study disclosed that there is only one method known for the synthesis of 3-acyl-1,2,4-benzothiadiazine-1,1-dioxide core. [20] In view of the broad range of biological activities and pharmaceutical importance of 1,2,4-benzothiadiazine-1,1-dioxides, we realized the scope to develop better and efficient process for their synthesis.…”

Section: Introductionmentioning

confidence: 99%

Tandem Protocol for the Synthesis of 3‐Acyl Benzothiadiazine 1,1‐Dioxides

et al. 2018

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A metal-free and efficient tandem synthesis of 3-acyl 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides and 3-acyl-2H-1,2,4-benzothiadiazine-1,1-dioxides has been developed via CÀH functionalization of ethynylarenes and ethenylarenes followed by condensation with 2-aminobenzenesulfonamide. The reaction involves the formation of arylglyoxal as an intermediate from multiform substrates through Kornblum oxidation in the presence of iodine and DMSO. Use of simple and readily available starting materials, inexpensive reagent, broad substrate scope and a very simple operation are noteworthy features of this protocol. This method provides an easy access to pharmaceutically important 3-acyl-1,2,4-benzothiadiazine-1,1-dioxides in good yields.

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ChemInform Abstract: Iodine‐Mediated Synthesis of 3‐Acylbenzothiadiazine 1,1‐Dioxides.

Zhang

Shi

et al. 2016

ChemInform

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Iodine-mediated synthesis of 3-acylbenzothiadiazine 1,1-dioxides

Abstract: SummaryAn iodine-mediated synthesis of 3-acylbenzothiadizine 1,1-dioxides is described. A range of electronically diverse acetophenones reacted well with several 2-aminobenzenesulfonamides, affording 3-acylbenzothiadiazine 1,1-dioxides in good yields.

Cited by 4 publications

References 35 publications

Metal‐Free Cross‐Dehydrogenative Coupling (CDC): Molecular Iodine as a Versatile Catalyst/Reagent for CDC Reactions

Metal‐Free Cross‐Dehydrogenative Coupling (CDC): Molecular Iodine as a Versatile Catalyst/Reagent for CDC Reactions

Tandem Protocol for the Synthesis of 3‐Acyl Benzothiadiazine 1,1‐Dioxides

ChemInform Abstract: Iodine‐Mediated Synthesis of 3‐Acylbenzothiadiazine 1,1‐Dioxides.

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