TCT-mediated click chemistry for the synthesis of nitrogen-containing functionalities: conversion of carboxylic acids to carbamides, carbamates, carbamothioates, amides and amines

Ahmed, Riyaz; Gupta, Ria; Akhter, Zaheen; Kumar, Mukesh; Singh, Parvinder Pal

doi:10.1039/d2ob00324d

Cited by 5 publications

(5 citation statements)

References 37 publications

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“… Substrate Substrate Product Time (min) Yield (%) a M.p. °C (Lit) 8 93 250 (250–251) 103 35 76 210 (199–202) 104 35 78 209 (204–206) 105 15 88 235 (233–237) 106 15 89 237 (230–235) 106 20 85 99–101 (93–94) 107 …”

Section: Resultsmentioning

confidence: 99%

Direct additive-free N-formylation and N-acylation of anilines and synthesis of urea derivatives using green, efficient, and reusable deep eutectic solvent ([ChCl][ZnCl2]2)

Abbasi,

Sardarian

2024

Sci Rep

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In the current report, we introduce a simple, mild efficient and green protocol for N-formylation and N-acetylation of anilines using formamide, formic acid, and acetic acid as inexpensive, nontoxic, and easily available starting materials just with heating along stirring in [ChCl][ZnCl2]2 as a durable, reusable deep eutectic solvent (DES), which acts as a dual catalyst and solvent system to produce a wide range of formanilides and acetanilides. Also, a variety of unsymmetrical urea derivatives were synthesized by the reaction of phenyl isocyanate with a range of amine compounds using this benign DES in high to excellent yields. [ChCl][ZnCl2]2 showed good recycling and reusability up to four runs without considerable loss of its catalytic activity.

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Section: Resultsmentioning

confidence: 99%

Direct additive-free N-formylation and N-acylation of anilines and synthesis of urea derivatives using green, efficient, and reusable deep eutectic solvent ([ChCl][ZnCl2]2)

Abbasi,

Sardarian

2024

Sci Rep

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“…In this direction, s-trichlorotriazine (TCT) is a well-known reagent and exploited well for synthesizing esters and amides. [30,31] Based on our previous experience, [31] we hypothesized that using TCT/NMM provides a better opportunity in term of cost and handling. The cost comparison of TCT and carbodiimide-based coupling reagents and bases are provided in Figure 3.…”

Section: Introductionmentioning

confidence: 99%

“…Considering the importance of these drugs, effective coupling conditions with ease of work‐up operation are highly required. In this direction, s ‐trichlorotriazine (TCT) is a well‐known reagent and exploited well for synthesizing esters and amides [30,31] . Based on our previous experience, [31] we hypothesized that using TCT/NMM provides a better opportunity in term of cost and handling.…”

Section: Introductionmentioning

confidence: 99%

TCT‐Mediated Process for the Preparation of Nafamostat Mesylate and Camostat Mesylate

et al. 2023

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The present work describes the s‐trichlorotriazine (TCT)‐mediated formation of highly functionalized ester‐based drugs, namely nafamostat mesylate and camostat mesylate. The TCT‐mediated activation of acids followed by the attack of a hydroxyl group (−OH group) resulted in the formation of ester. The high aqueous solubility of cyanuric acid eases the work‐up process and avoids repetitive washing process (better E‐factor). The present method also avoids using pyridine as a base, and instead of that, N‐methylmorpholine (NMM) was used for the coupling. Moreover, we have also demonstrated the synthesis of key intermediates namely, 4‐guanidinobenzoic acid and 6‐hydroxy‐2‐naphthimidamide from economical and readily available raw materials. The TCT‐mediated coupling provides many advantages in scalability, cost‐effectiveness and environmental friendly handling.

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“…[1][2][3][4][5] These functional groups are typically accessed from carboxylic acids, or derivatives thereof, via isocyanate intermediates. 6 In the context of polymer synthesis and functionalisation, the importance of isocyanates cannot be understated. For example, diisocyanates are required for the synthesis of polyureas and polyurethanes which have global market values in the region $1 billion and $75 billion USD respectively.…”

mentioning

confidence: 99%

“…1–5 These functional groups are typically accessed from carboxylic acids, or derivatives thereof, via isocyanate intermediates. 6…”

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confidence: 99%

An electrochemical Hofmann rearrangement on acrylamide copolymers

Wang

Wilson

2023

Polym. Chem.

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TCT-mediated click chemistry for the synthesis of nitrogen-containing functionalities: conversion of carboxylic acids to carbamides, carbamates, carbamothioates, amides and amines

Abstract: Here, we report a s-trichlorotriazine mediated one-pot general method for the conversion of carboxylic acids into ubiquitous functionalities such as carbamides, carbamates, carbamothioates, amides, and amines.

Cited by 5 publications

References 37 publications

Direct additive-free N-formylation and N-acylation of anilines and synthesis of urea derivatives using green, efficient, and reusable deep eutectic solvent ([ChCl][ZnCl2]2)

Direct additive-free N-formylation and N-acylation of anilines and synthesis of urea derivatives using green, efficient, and reusable deep eutectic solvent ([ChCl][ZnCl2]2)

TCT‐Mediated Process for the Preparation of Nafamostat Mesylate and Camostat Mesylate

An electrochemical Hofmann rearrangement on acrylamide copolymers

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