A cis Amide Bond Surrogate Incorporating 1,2,4‐Triazole.

Abstract

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New Synthetic Routes to Triazolo-benzodiazepine Analogues: Expanding the Scope of the Bump-and-Hole Approach for Selective Bromo and Extra-Terminal (BET) Bromodomain Inhibition

“…However, the reaction did not proceed due to the poor solubility of 21 in pyridine at rt (Table 1, entry 3). Despite its poor solubility, activation of the thioamide with thiophilic mercury diacetate 34 allowed for rapid and quantitative consumption of 21 at rt and afforded the intermediate acylhydrazone almost quantitatively along with trace amount of product 22 (Table 1, entry 4). Switching the solvent to acetonitrile led to similar results, even after reaction times up to 6 days (Table 1, entry 5).…”

1,5-Disubstituted 1,2,3-Triazoles as Amide Bond Isosteres Yield Novel Tumor-Targeting Minigastrin Analogs

“…Disubstituted tetrazoles as well as 1,2,4-and 1,2,3-triazoles are among the heterocycles that allow a precise replacement of an amide bond (Figure 1). [7][8][9] Triazole synthesis can be performed in solution or on solid support, the latter making their use particularly appealing for peptide chemists. [10][11][12] In this context, 1,2,3-triazoles (Tz) are the only heterocycles that, while having a similar dipolar moment, are capable of mimicking both trans-and cis-amide bonds, depending on their 1,4-or 1,5-substitution pattern, respectively, while being synthetically accessible (Figure 2).…”

A facile, practical and metal-free microwave-assisted protocol for mono- and bis-[1,2,4]triazolo[1,5-a]pyridines synthesis utilizing 1-amino-2-imino-pyridine derivatives as versatile precursors

“…2-Methyl-7-phenyl [1,2,4] General procedure for the preparation of triazolo[1,5-a] pyridine derivatives (5l-z and [11][12][13][14]. Independent mixtures of 1-amino-2-imino-pyridine 3a-e (3.0 mmol), and the appropriate reactant (3.0 mmol) in ethanol (10.0 mL) containing acetic acid (0.90 g, 5 equiv.…”

“…7 In addition examples of these compounds have been utilized as herbicidal agents 8 and for treatment of diabetes (type-II), 9,10 cardiovascular disorders, 11 and hyperproliferative disorders. 12 Besides, such derivatives have been included in a variety of pharmaceutically effective compounds as dipeptidomimetics 13 and have been employed as effective ligands for various transition metals. [14][15][16] As a consequence of the above-mentioned applications, several approaches for the triazolopyridine assembly have been established over the past decades.…”