Recent developments in benzotriazole methodology for construction of pharmacologically important heterocyclic skeletons

Kale, Raju R.; Prasad, Virendra; Mohapatra, Prabhu P.; Tiwari, Vinod K.

doi:10.1007/s00706-010-0378-1

Cited by 65 publications

(20 citation statements)

References 123 publications

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“…[1][2][3][4][5][6][7][8][9] N-acylbenzotriazoles are one of the most useful benzotriazolederivatives which have been successfully utilized to prepare numerous biologically relevant compounds under neutral and mild conditions by N-, C-, S-, and O-acylations. [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] In recent years our group has been involved in exploration of the synthetic utility of N-acylbenzotriazoles to make sugar amides by N-acylation, 25 benzoxazoles and N-phenylamides by benzotriazole ring cleavage 26,27 and ureas, carbamates and thiocarbamates by the Curtius rearrangement.…”

Section: Introductionmentioning

confidence: 99%

A new methodology for the synthesis of N-acylbenzotriazoles

Singh¹,

Agrahari²,

Singh³

et al. 2017

Arkivoc

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Dedicated to the late Prof. Alan R Katritzky for his excellent contributions to benzotriazole chemistryReceived 04-07-2017Accepted 06-28-2017 Published on line 07-21-2017 AbstractA facile and economic path for an easy access of diverse N-acylbenzotriazoles from carboxylic acid has been devised using NBS/PPh3 in anhydrous dichloromethane. High yield of product was obtained at room temperature in one hour reaction time under mild reaction conditions.

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Section: Introductionmentioning

confidence: 99%

A new methodology for the synthesis of N-acylbenzotriazoles

Singh¹,

Agrahari²,

Singh³

et al. 2017

Arkivoc

Self Cite

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“…With the appearance of pathogens resistant to common azole‐based pharmaceuticals, benzotriazoles emerged as valuable substitutes and since have been employed for antibacterial, antifungal, and antiviral agents with remarkable potency [4c–f,6] . Therefore, rapid and scalable access to a broad range of functionalized benzotriazoles could further support medicinal studies.…”

Section: Methodsmentioning

confidence: 99%

Scalable Synthesis of Benzotriazoles via [3+2] Cycloaddition of Azides and Arynes in Flow

et al. 2021

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A method for the metal‐free synthesis of benzotriazoles in flow is reported. Using azides and in situ generated arynes, benzotriazoles are formed in a [3+2] cycloaddition within minutes. Employing different substitution patterns of the azide and aryne coupling partners, a modular access to benzotriazoles is provided. Thermal strain of hazardous azides and accumulation of reactive intermediates is minimized by short reaction times in flow, improving the safety profile of the process. The scalability of the reaction is demonstrated.

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“…Besides this, easy availability, low cost, and nontoxic nature of benzotriazole moiety enhance the economic and environment friendly nature of chemical reactions employing benzotriazole methodology. [1][2][3] Recently, N-acylbenzotriazole derivatives have emerged as an alternative to acid chlorides in N-, O-, S-, and C-acylations under mild and neutral conditions for the synthesis of amides, acid azides, peptides, oxazolines, esters, diketones, and thiazolines. [4][5][6][7][8][9][10][11][12][13][14][15][16][17] Furthermore, long time stability on storage, moisture insensitivity, and physical state (generally solid) also make it a suitable substitute of acid chlorides for the common laboratory reactions.…”

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confidence: 99%