One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water

Rao, Mugada Sugunakara; Hussain, Sahid

doi:10.1016/j.tetlet.2021.153159

Cited by 5 publications

(3 citation statements)

References 104 publications

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“…The authors have cited additional references within the Supporting Information. [53][54][55][56][57][58]…”

Section: Experimental Section Preparation Of Catalystsmentioning

confidence: 99%

One‐pot Tandem Synthesis and Spontaneous Product Separation of N‐heterocycles based on Bifunctional Small‐molecule Photocatalyst

Yao,

Jia,

Miao

et al. 2024

ChemSusChem

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Homogeneous and heterogeneous reactions wherein the resulting products remain dissolved in solvents generally require complicated separation and purification process, despite the advantage of heterogeneous systems allowing retrieval of catalysts. Herein, we propose an efficient approach for the one‐pot tandem synthesis of quinazolines, quinazolinones and benzothiadiazine 1,1‐dioxides from alcohols and amines utilizing a bifunctional bipyridiniun photocatalyst with redox and Lewis acid sites with air as an oxidant. Through solvent‐modulation strategy, the photocatalytic system exhibits high performance and enables most products to separate spontaneously. Consequently, the homogeneous catalyst can be reused by direct centrifugation isolation of the products. Notably, the method is also applicable to the less active substrates, such as heterocyclic alcohols and aliphatic alcohols, and thus provides an efficient and environmentally friendly photocatalytic route with spontaneous separation of N‐heterocycles to reduce production costs and meet the needs of atomic economy and green chemistry.

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“…The authors have cited additional references within the Supporting Information. [53][54][55][56][57][58]…”

Section: Experimental Section Preparation Of Catalystsmentioning

confidence: 99%

One‐pot Tandem Synthesis and Spontaneous Product Separation of N‐heterocycles based on Bifunctional Small‐molecule Photocatalyst

Yao,

Jia,

Miao

et al. 2024

ChemSusChem

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“…Nitrogen–sulfur heterocyclic compounds have garnered substantial attention from practitioners in the field of organic chemistry for an extended period due to their multifarious significance in the realms of natural products, advanced materials, and the rational design of bioactive agents employed for diverse pharmaceutical exigencies . Among these compounds, 3,4-dihydro-benzothiadiazine 1,1-dioxides, for example aquamox, thiabutazide, bendroflumethiazide, cyclothiazide, IDRA-21, and BPAM538 (Figure ), are often used as effective diuretics for the treatment of high blood pressure and have also been found to interact with both sites of the GluA2-LBD dimer interface . Considering their remarkable significance, enormous efforts have been devoted to efficient and convenient strategies for constructing 3,4-dihydro-benzothiadiazine 1,1-dioxide skeletons.…”

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confidence: 99%

Palladium-Catalyzed Aminosulfonylation of ortho-Iodoanilines with the Insertion of Sulfur Dioxide for the Synthesis of 3,4-Dihydro-benzothiadiazine 1,1-Dioxides

Qi,

Wen,

Hao Li

et al. 2023

Org. Lett.

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A simple and efficient Pd-catalyzed oxidative cyclization system is developed for the chemo-and regioselective synthesis of 3,4-dihydro-benzothiadiazine 1,1-dioxides, which are formed through aminosulfonylation of ortho-iodoanilines with SO 2 . DABSO is utilized as the source of SO 2 , and the organic compound O 2 acts as an oxidant. This direct C−S, S−N, and C−N functionalization is highly efficient, and broad functional group tolerance is observed, resulting in moderate to excellent yields of 3,4dihydro-benzothiadiazine 1,1-dioxides. Furthermore, this method is amenable to gram-scale synthesis.

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“…Similarly, IDRA-21 is a modulator of the AMPK receptor and has been found to exert nootropic effects that improve cognitive abilities in animal studies (Figure ). Conventionally, the 3,4-dihydro-benzothiadiazine-1,1-dioxides have been prepared by condensation of aldehydes with 2-aminobenzenesulfonamides under metal-catalyzed, metal-free catalytic or even noncatalytic reaction conditions. − Other approaches involve the use of aldehyde precursors such as benzyl alcohols, − arylacetic acids, benzylamines, and methylarenes. , The existing processes invariably use 2-aminobenzenesulfonamides as one of the starting materials, which obviously are prepared by the reduction of the corresponding 2-nitrobenzenesulfonamides. As nitro compounds are feedstock chemicals, their reductive transformations to the synthesis of important nitrogen heterocycles could present an attractive synthetic strategy.…”

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confidence: 99%

Dithionite-Mediated Tandem Nitro Reduction/Imine Formation/Intramolecular Cyclization for the Synthesis of Dihydro-benzothiadiazine-1,1-dioxides

Laha,

Gupta,

Hazra

2023

J. Org. Chem.

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A one-pot, tandem reductive annulation of 2nitrobenzenesulfonamides with aldehydes to the synthesis of substituted 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides in the presence of sodium dithionite (Na 2 S 2 O 4 ) is reported under mild conditions. The method involves in situ reduction of the nitro group followed by condensation with aldehydes to form an imine, which upon subsequent intramolecular cyclization forms the product under one-pot conditions. The protocol features use of inexpensive Na 2 S 2 O 4 as the exclusive reagent, appreciable functional group tolerance, broad substrate scope, high product yields, and scalability.

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One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water

Cited by 5 publications

References 104 publications

One‐pot Tandem Synthesis and Spontaneous Product Separation of N‐heterocycles based on Bifunctional Small‐molecule Photocatalyst

One‐pot Tandem Synthesis and Spontaneous Product Separation of N‐heterocycles based on Bifunctional Small‐molecule Photocatalyst

Palladium-Catalyzed Aminosulfonylation of ortho-Iodoanilines with the Insertion of Sulfur Dioxide for the Synthesis of 3,4-Dihydro-benzothiadiazine 1,1-Dioxides

Dithionite-Mediated Tandem Nitro Reduction/Imine Formation/Intramolecular Cyclization for the Synthesis of Dihydro-benzothiadiazine-1,1-dioxides

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