Ethyl 5-Formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and DFT Calculation

Abstract

For the first time, 5-formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate was synthesized via a two-step scheme. The molecular structure of the compound was determined by a single-crystal X-ray diffraction analysis. The Hirshfeld surface analysis was used to study various intermolecular interactions. The crystalline structure is marked by the presence of three types of π-interactions (n→π*, lp···π, and π···π) between the -C(H)=O group and triazole rings. The compound is a versatile polyfunctional building block for construction of annulated 1,2,3-triazoles.

Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1H-1,2,3-triazole-4-carboxylic Acids Series

“…Recently, we have developed a convenient synthetic route to ethyl 1-(het)aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates [1][2][3]. Moreover, in our latest article in this journal [3], structural features of 5-formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate as a representative of such series were set out, and a synthetic application of ortho-formyl (hetero)aromatic carboxylic acids in the synthesis of numerous classes of important molecules was emphasized (see ref. [3] and works cited therein).…”

“…Moreover, in our latest article in this journal [3], structural features of 5-formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate as a representative of such series were set out, and a synthetic application of ortho-formyl (hetero)aromatic carboxylic acids in the synthesis of numerous classes of important molecules was emphasized (see ref. [3] and works cited therein). The wide synthetic application of ortho-formyl (hetero)aromatic carboxylic acids is still growing as confirmed by the newly published article [4].…”