The Synthesis of Some New (S)-1-Aryl-N-(1-hydroxy-3-phenylpropan-2-yl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

Abstract

Some new (S)‐1‐aryl‐N‐(1‐hydroxy‐3‐phenylpropan‐2‐yl)‐5‐methyl‐1 H‐1,2,3‐triazole‐4‐carboxamides 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j have been synthesized and established by 1H and 13C NMR, IR, MS spectra, CHN analyses, and x‐ray diffraction crystallography. The molecular conformation and packing is stabilized by interactions of intermolecular H‐bond O2’‐H2'···O1, O2‐H2···O1’ and intramolecular H‐bond N4’‐H4'N···N3’, N4’‐H4'N···O2’, N4‐H4N···N3, N4‐H4N···O2. The two rings of five numbers were formed by H‐bond in a molecular.

Synthesis, crystal structure and Hirshfeld surface analysis of 5-cyclopropyl-N-(2-hydroxyethyl)-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carboxamide

“…most closest related compounds containing a similar 1-aryl-1H-1,2,3-triazole-4-carboxamide skeleton to the title compound but with different substituents on the amide are: N-(4-chlorophenyl)-5-cyclopropyl-1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxamide(Pokhodylo & Slyvka et al, 2020), (S)-1-(4-chlorophenyl)-N-(1-hydroxy-3-phenylpropan-2-yl)-5-methyl-1H-1,2,3-triazole-4-carboxamide (I)[Cambridge Structural Database (Version 2021.1;Groom et al, 2016) refcode ZIPSEY;Shen et al, 2013], 1-(4-chlorophenyl)-5-methyl-N-[(3-phenyl-1,2-oxazol-5-yl)methyl]-1H-1,2,3-triazole-4-carboxamide (II) (LELHOB;Niu et al, 2013), (5-methyl-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-1,2,3-triazol-4-yl)morpholino)methanone (III) (LOHWIP;Anuradha et al, 2008) and 1-(3-amino-5-(3-hydroxy-3-methylbut-1-yn-1yl)phenyl)-N-butyl-1H-1,2,3-triazole-4-carboxamide (IV) (BEBJEZ;Li et al, 2012).Compounds (I) and (II) crystallize in the monoclinic crystal system with space groups P2 1 and P2 1 /c, respectively, while compounds (III) and (IV) crystallize in the triclinic space group P1. Structure (I) contains two crystallographically independent molecules, the hydroxyl groups of which participate in intermolecular O-HÁ Á ÁO hydrogen bonds.…”