One-Pot, Three-Component Reaction Using Modified Julia Reagents: A Facile Synthesis of 4,5-Disubstituted 1,2,3-(NH)-Triazoles in a Wet Organic Solvent

Abstract

A new one-pot, three component reaction involving the use of Julia reagent, aldehyde, and sodium azide was developed for the efficient synthesis of N-unsubstituted 1,2,3-triazoles. This reaction could be carried out under mild reaction conditions without any precaution, and broad scope of substrates, both respect to Julia reagents and aldehydes, could be applied in this reaction system in generation of a small library of title compounds.

Metal‐Free Multicomponent Reaction for Synthesis of 4,5‐Disubstituted 1,2,3‐(NH)‐Triazoles

“…As two‐carbon synthons, olefinic sulfur salts act as electrophiles in [2+1]‐cycloadditions to form three‐membered cyclic compounds, [2+3]‐cycloadditions to form cyclopropane‐, epoxide‐, or aziridine‐fused heterocycles, or [2+4]‐cycloadditions to form six‐membered ring compounds (Scheme b) . We envision that the electron‐deficient double bond in olefinic sulfur salts like Julia‐type reagent, nitroalkene, and acyl acetonitrile possibly undergoes [2+3]‐cycloaddition to azide ions to form a 4,5‐disubstituted‐1,2,3‐( NH )‐triazole (Scheme , c).…”

“…Thus, a proposed mechanism for this domino reaction is described in Scheme . In the presence of L ‐proline, sulfur salt I is transformed into a key intermediate, olefinic sulfonium salt II , via the Knoevenagel condensation reaction ,. The electron deficiency of dipolarophile II lowers the energy level of its lowest unoccupied molecular orbital (LUMO) and causes ready 1,3‐dipolar cycloaddition between II and azide ion to produce the final 1,2,3‐( NH )‐triazole…”

Aluminium(III) Chloride‐Catalyzed Three‐Component Condensation of Aromatic Aldehydes, Nitroalkanes and Sodium Azide for the Synthesis of 4‐Aryl‐NH‐1,2,3‐triazoles

“…In 2008, the Shi group reported a proline‐catalyzed three‐component reaction of aldehyde, β‐alkylnitroalkene, and NaN 3 to synthesize 4,5‐disubstituted‐1,2,3‐ NH ‐triazoles 18. Then, a three‐component reaction based upon the Julia reagent, aldehyde, and NaN 3 was conducted by the Chu group 19. Lately, Lin developed another three‐component reaction based upon aldehyde, nitroalkane and NaN 3 20.…”

“…It was exciting that the reactions resulted in high efficiency, which gave the ester group‐substituted NH ‐1,2,3‐triazoles with high yields. So far, this method is the optimal way to synthesize ester group‐substituted NH ‐1,2,3‐triazoles 19,24…”

Recyclable Acid–Base Bifunctional Core–Shell–Shell Nanosphere Catalyzed Synthesis of 5‐Aryl‐1H‐1,2,3‐triazoles through the “One‐Pot” Cyclization of Aldehydes, Nitromethane, and Sodium Azide

“…[9] After that, at hree-component reactionb ased upon the Julia reagent,a ldehydes,a nd NaN 3 was reported. [10] Recently,L in and Chen individually developed three-component reactions involving aldehydes, nitroalkanes, and NaN 3 in the presence of excessa mounts of NaHSO 3 / Na 2 SO 3 [11] and ac atalytic amount of aluminum(III)c hloride. [12] These resultsn ot only make the synthesis of 1H-1,2,3-triazoles easier,b ut they also revealt hat the three-componentc ondensation may be an acid-catalyzed process.…”