Visible-light driven regioselective synthesis of 1<i>H</i>-tetrazoles from aldehydes through isocyanide-based [3 + 2] cycloaddition

Verma, Fooleswar; Sahu, Asha; Singh, Puneet Kumar; Rai, Ankita; Singh, Manorama; Vijai, K.

doi:10.1039/c8gc01321g

Cited by 36 publications

(13 citation statements)

References 110 publications

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“…The azide not only behaves as three-nitrogen donor of tetrazole ring but also it converts the aldehyde into isocyanide. 130…”

Section: Tetrazoles Through Non-multicomponent Reaction Routesmentioning

confidence: 99%

“…The azide not only behaves as three-nitrogen donor of tetrazole ring but also it converts the aldehyde into isocyanide. 130 Elaborating the above-mentioned reaction, Domling et al 125 treated the N-substituted 2-isocyanoacetamides 131 22 with trimethylsilyl azide with 25% cosolvent water in methanol at rt. A library of 18 1-substituted-1H-tetrazoles 23 was efficiently synthesized as most of the final products were precipitated during workup (Scheme 6).…”

Section: Tetrazoles Through Non-multicomponent Reaction Routesmentioning

confidence: 99%

“…The reaction is often performed in methanol, however, 2,2,2-trifluoroethanol or biphasic water chloroform mixtures were also reported. 136−139 Recently, an ultrasound accelerated UT-4CR was described without solvent 6 Ser 130 and Ser 237 form each a hydrogen bond to the tetrazole −N2 and −N5 via their side chain −OH at 2.8 and 2.7 Å, respectively. N-3 is in a 2.7 Å contact to the side chain −OH of Thr.…”

Section: Monocyclic Tetrazoles Derivativesmentioning

confidence: 99%

“…Example of a tetrazolyl ( 3 ) forming four hydrogen bonds (PDB 4DE1). Ser and Ser form each a hydrogen bond to the tetrazole −N2 and −N5 via their side chain −OH at 2.8 and 2.7 Å, respectively. N-3 is in a 2.7 Å contact to the side chain −OH of Thr .…”

Section: Introductionmentioning

confidence: 99%

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Tetrazoles via Multicomponent Reactions

2019

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Tetrazole derivatives are a prime class of heterocycles, very important to medicinal chemistry and drug design due to not only their bioisosterism to carboxylic acid and amide moieties but also to their metabolic stability and other beneficial physicochemical properties. Although more than 20 FDA-approved drugs contain 1H- or 2H-tetrazole substituents, their exact binding mode, structural biology, 3D conformations, and in general their chemical behavior is not fully understood. Importantly, multicomponent reaction (MCR) chemistry offers convergent access to multiple tetrazole scaffolds providing the three important elements of novelty, diversity, and complexity, yet MCR pathways to tetrazoles are far from completely explored. Here, we review the use of multicomponent reactions for the preparation of substituted tetrazole derivatives. We highlight specific applications and general trends holding therein and discuss synthetic approaches and their value by analyzing scope and limitations, and also enlighten their receptor binding mode. Finally, we estimated the prospects of further research in this field.

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“…The azide not only behaves as three-nitrogen donor of tetrazole ring but also it converts the aldehyde into isocyanide. 130…”

Section: Tetrazoles Through Non-multicomponent Reaction Routesmentioning

confidence: 99%

Section: Tetrazoles Through Non-multicomponent Reaction Routesmentioning

confidence: 99%

Section: Monocyclic Tetrazoles Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Tetrazoles via Multicomponent Reactions

2019

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“…There are many examples of isonitriles in multicomponent reactions for forming original biologically-active compounds [1,2]. They are widely used in green chemistry [3,4,5] and in the synthesis of tetrazoles [6,7,8,9,10,11]. Substituted or heterocyclic annulated tetrazoles have an extensive range of biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes

et al. 2018

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1-(p-Methoxyphenyl)tetrazolyl-substituted 6,7-dimethoxy(6,7-methylenedioxy)-1,2,3,4-tetrahydroisoquinolines formed tetrazolyl-substituted azocines in high yields by using activated alkynes. Unsubstituted at 6,7,8-aromatic fragment 1-tetrazolylisoquinoline interacted in several pathways forming tetrazolyl-substituted azocines, 1-tetrazolyl-1-R-vinylisoquinolines and 3-azaspiro[5.5]undeca-1,7,9-triene.

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Photocatalytic C(sp³)−H Activation towards α‐methylenation of Ketones using MeOH as 1 C Source Steering Reagent

et al. 2019

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Unprecedented direct access to terminal enones via a-methylenation of aryl ketones to form C=C bond is achieved under visible-light conditions using methanol as one carbon source substrate and solvent as well. The reaction involves Cu@g-C 3 N 4catalysed in situ oxidation of methanol into formaldehyde followed by dehydrative cross aldol type reaction. Various aryl ketones react efficiently with MeOH, producing a,b-unsaturated carbonyl compounds only in 4-8 h at room temperature in excellent yield (84-97%). Operational simplicity, wide substrate scope, ambient reaction conditions, visible-light photocatalysis and novel application of MeOH as methylene donor substrate are the salient features making the envisaged protocol mild, efficient and green alternative to the existing methods for synthesis of such fine chemicals.

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Visible-light driven regioselective synthesis of 1H-tetrazoles from aldehydes through isocyanide-based [3 + 2] cycloaddition

Abstract: A novel and green Co@g-C3N4 catalyzed visible light driven direct regioselective synthesis of 1H-tetrazoles directly from various aldehydes and sodium azide is reported.

Cited by 36 publications

References 110 publications

Tetrazoles via Multicomponent Reactions

Tetrazoles via Multicomponent Reactions

Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes

Photocatalytic C(sp³)−H Activation towards α‐methylenation of Ketones using MeOH as 1 C Source Steering Reagent

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Visible-light driven regioselective synthesis of 1H-tetrazoles from aldehydes through isocyanide-based [3 + 2] cycloaddition

Abstract: A novel and green Co@g-C3N4 catalyzed visible light driven direct regioselective synthesis of 1H-tetrazoles directly from various aldehydes and sodium azide is reported.

Cited by 36 publications

References 110 publications

Tetrazoles via Multicomponent Reactions

Tetrazoles via Multicomponent Reactions

Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes

Photocatalytic C(sp3)−H Activation towards α‐methylenation of Ketones using MeOH as 1 C Source Steering Reagent

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Photocatalytic C(sp³)−H Activation towards α‐methylenation of Ketones using MeOH as 1 C Source Steering Reagent