91165-89-8

Upstream product

• 6921-40-0 1-azidonaphthalene 
• 34846-90-7 methyl 3-methoxyprop-2-enoate 
• 67-56-1 methanol 
• 107-02-8 acrolein 
• 1189781-14-3 C₈H₁₁N₃O₂ 
• 922-67-8 propynoic acid methyl ester 
• 91165-90-1 ethyl 1-(1-naphthyl)-1H-1,2,3-triazole-4-carboxylate 

Relevant academic research and scientific papers

Catalytic Intermolecular Cross-Couplings of Azides and LUMO-Activated Unsaturated Acyl Azoliums

An example for the catalytic synthesis of densely functionalized 1,2,3-triazoles through a LUMO activation mode has been developed. The protocol is enabled by intermolecular cross-coupling reactions of azides with in situ-generated α,β-unsaturated acyl az

Direct access to 1,4-disubstituted 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of α,β-unsaturated esters with azides

DBU-catalyzed organocatalytic 1,3-dipolar cycloaddition reactions of α,β-unsaturated esters with azides have been developed. This strategy generates 1,4-disubstituted 1,2,3-triazoles in high yields with high regioselectivities. It is demonstrated that some of these products can be transformed into important pharmaceutical agents.

'Click' chemistry on sugar-derived alkynes: A tandem 'click-click' approach to bistriazoles

Development of a tandem 'click-click' approach to the formation of successive 1,4-disubstituted 1,2,3-triazole linkages and 'click chemistry' on sugar-derived alkynes are described. Georg Thieme Verlag Stuttgart.

Photolysis of 1-Aryl-1,2,3-triazoles; Rearrangement via !H-Azirines

The preparation and photolysis of a series of 1-(1-naphthyl)-1,2,3-triazoles, (2)-(5), and of 1-(2-methyl-1-naphthyl)-1,2,3-triazoles, (6)-(9), with and without electron-withdrawing groups (CO2R, CONH2, CN, CHO, COPh) in the triazole ring, are described.In the first series, triazoles (3) with two electron-withdrawing groups, and triazoles (4) with one such group at C-4, mostly give good yields of the expected benzindoles (10) and 11 respectively.Triazoles (5) with the electron-withdrawing group at C-5 also give benzindoles but these are now mixtures of the expected (12) and rearranged indoles (11).Photolysis of the 1-phenyltriazoles (21) and (22) follows the same pattern, those with the electron-withdrawing group at C-5 rearranging to give mixtures of indoles (23) and (24).This is explained by a mechanism (Scheme 3) in which the less stable carbene intermediate (13) rearranges to the more stable carbene (15) via the 1H-azirine (14), in competition with its direct cyclisation.This provides the first evidence for antiaromatic 1H-azirines as intermediates in a photochemical reaction.Photolysis of the 2-methylnaphthyl compounds follows a different path: diester (7b) and dinitrile (7d) give high yields of the deeply coloured 9-methyl-1H-benzoquinoline derivatives (25a) and (25b) respectively, the first stable examples of this ring system to be isolated.Photolysis of the nitrile (8c) gives 9b-methyl-9bH-benzindole-3-carbonitrile (28), a rare example of a stable indole with a ring junction substituent. 1,2-Shifts in the carbenes are only observed with the bis(trimethylsilyl)triazoles (2d) and (6f), in keeping with the known rapid migration of trimethylsilyl groups to carbene centres.

Syntheses and Spectroscopic Studies of 1,8-Bistriazolylnaphthalenes

The first 1,8-diheterocyclic naphthalenes, the 1,8-bis(1'H-1',2',3'-triazolyl)naphthalenes (1a - i), have been synthesized by 1,3-dipolar cycloadditions of 1,8-diazidonaphthalene to acetylenic esters or enolates of acetoacetic esters, and have strained structures as revealed by comparison of their spectral properties with those of the corresponding 1-(1'H-1',2',3'-triazolyl)naphthalenes.