55848-63-0Relevant academic research and scientific papers
Regioselective reduction of 1h-1,2,3-triazole diesters
Butler, Christopher R.,Bendesky, Justin,Schoffstall, Allen Milton
, (2021/09/24)
Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.
Mn-Catalyzed Highly Efficient Aerobic Oxidative Hydroxyazidation of Olefins: A Direct Approach to β-Azido Alcohols
Sun, Xiang,Li, Xinyao,Song, Song,Zhu, Yuchao,Liang, Yu-Feng,Jiao, Ning
, p. 6059 - 6066 (2015/05/27)
(Chemical Equation Presented). An efficient Mn-catalyzed aerobic oxidative hydroxyazidation of olefins for synthesis of β-azido alcohols has been developed. The aerobic oxidative generation of azido radical employing air as the terminal oxidant is disclosed as the key process for this transformation. The reaction is appreciated by its broad substrate scope, inexpensive Mn-catalyst, high efficiency, easy operation under air, and mild conditions at room temperature. This chemistry provides a novel approach to high value-added β-azido alcohols, which are useful precursors of aziridines, β-amino alcohols, and other important N- and O-containing heterocyclic compounds. This chemistry also provides an unexpected approach to azido substituted cyclic peroxy alcohol esters. A DFT calculation indicates that Mn catalyst plays key dual roles as an efficient catalyst for the generation of azido radical and a stabilizer for peroxyl radical intermediate. Further calculation reasonably explains the proposed mechanism for the control of C-C bond cleavage or for the formation of β-azido alcohols.
Synthesis of hybrid 1,2,3-triazolo-δ-lactams/lactones using Huisgen [3+2] cycloaddition 'click-chemistry' in water
Kumar, Indresh,Rana, Sravendra,Cho, Jae Whan,Rode, Chandrashekhar V.
experimental part, p. 352 - 355 (2010/06/16)
The synthesis of a new class of hybrid 1,2,3-triazozlo-δ-lactams/lactones has been achieved using the Huisgen [3+2] dipolar cycloaddition 'click-chemistry' reaction of various organic azides with an activated alkyne in water, followed by cyclization.
A SILYL-FUNCTIONALIZED ALKYL AZIDE, TRIMETHYLSILYLMETHYL AZIDE; SYNTHESIS AND CYCLOADDITION REACTION TO ACETYLENIC DIPOLAROPHILES
Tsuge, Otohiko,Kanemasa, Shuji,Matsuda, Koyo
, p. 1131 - 1134 (2007/10/02)
Thermally stable trimethylsilylmethyl azide was first synthesized from the reaction of chloromethyltrimethylsilane with sodium azide.Its use as an α-functionalized synthetic equivalent of methyl azide was demonstrated in the reaction with acetylenic dipol
