57294-86-7Relevant academic research and scientific papers
Regiospecific synthesis of 2-allylated-5-substituted tetrazoles via palladium-catalyzed reaction of nitriles, trimethylsilyl azide, and allyl acetates
Gyoung, Young Soo,Shim, Jae-Goo,Yamamoto, Yoshinori
, p. 4193 - 4196 (2000)
A variety of 2-allylated-5-substituted tetrazoles were prepared in excellent yields through the reaction of alkyl and arylidenemalononitriles, allyl acetates and trimethylsilyl azide in the presence of a palladium catalyst. (C) 2000 Elsevier Science Ltd.
Interrupted CuAAC-Thiolation for the Construction of 1,2,3-Triazole-Fused Eight-Membered Heterocycles from O-/N-Propargyl derived Benzyl Thiosulfonates with Organic Azides
Jannapu Reddy, Raju,Waheed, Md.,Haritha Kumari, Arram,Rama Krishna, Gamidi
supporting information, p. 319 - 325 (2021/12/02)
A copper(I)-catalyzed interrupted click-sulfenylation of O-/N-propargyl benzyl thiosulfonates with organic azides has been disclosed. The unified CuAAC-thiolation provides a wide range of triazole-fused eight-membered heterocycles in good to high (51–94%) yields under mild reaction conditions. Moreover, a three-component reaction is also achieved involving O-/N-propargyl benzyl thiosulfonates, benzyl bromide, and sodium azide to deliver fused-triazoles in 61–74% yields. From a synthetic point of view, the present protocol has been demonstrated at gram-scale reactions. A plausible mechanism is also proposed based on experimental results and control experiments. (Figure presented.).
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.
Further investigation of harmicines as novel antiplasmodial agents: Synthesis, structure-activity relationship and insight into the mechanism of action
Marinovi?, Marina,Poje, Goran,Perkovi?, Ivana,Fontinha, Diana,Prudêncio, Miguel,Held, Jana,Pessanha de Carvalho, Lais,Tandari?, Tana,Vianello, Robert,Raji?, Zrinka
, (2021/07/19)
The rise of the resistance of the malaria parasite to the currently approved therapy urges the discovery and development of new efficient agents. Previously we have demonstrated that harmicines, hybrid compounds composed from β-carboline alkaloid harmine
Highly selective hydrosilylation of equilibrating allylic azides
Liu, Ruzhang,Liu, Yongmei,Wang, Juan,Wei, Zhen,Xue, Huaiguo
supporting information, p. 5038 - 5041 (2020/05/18)
The Pt-catalyzed hydrosilylation of equilibrating allylic azides is reported. The reaction provides only one out of four possible hydrosilylation products in good yields and with very high chemoselectivity (alk-1-enevs.alk-2-ene), regioselectivity (linearvs.branched), and excellent functional group tolerance.
Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis
Braga, Felipe C.,Gallou, Fabrice,Lee, Nicholas R.,Lippincott, Daniel J.,Lipshutz, Bruce H.,Moghadam, Farbod A.,Zhu, Bingchun
, (2020/07/15)
Palladium-catalyzed allylic substitution, or "Tsuji-Trost"reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N-H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.
Reactions of α-haloacroleins with azides: Highly regioselective synthesis of formyl triazoles
Zhang, Dongsheng,Fan, Yingzhu,Yan, Zhongliang,Nie, Yi,Xiong, Xingquan,Gao, Lizhu
supporting information, p. 4211 - 4216 (2019/08/07)
A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H2O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting triazoles exhibited an aldehyde group at the C4 position and demonstrated synthetic utilizations. One 1,2,3-triazole compound containing diastereotopic protons was also identified.
Palladium-Catalyzed Annulation of Aryltriazoles and Arylisoxazoles with Alkynes
Yuan, Hairui,Wang, Min,Xu, Zhenghu,Gao, Hongyin
supporting information, p. 4386 - 4392 (2019/08/12)
We developed herein a palladium-catalyzed annulation of aryltriazoles and arylisoxazoles with internal alkynes via C?H bond activation process. 4,5-disubstituted-3H-naphtho[1,2-d][1,2,3]triazoles and 4,5-disubstituted-naphtho[2,1-d]isoxazoles could be afforded in good yields, respectively. The starting materials are readily available and the scope and applications of this transformation were explored. The reaction offers a practical approach to naphthalene fused heterocycles. (Figure presented.).
Practical regio- and stereoselective azidation and amination of terminal alkenes
Ojo, Olatunji S.,Miranda, Octavio,Baumgardner, Kyle C.,Bugarin, Alejandro
supporting information, p. 9354 - 9358 (2019/01/03)
There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields.
Regiocontrolled Wacker Oxidation of Cinnamyl Azides
Carlson, Angela S.,Calcanas, Cristian,Brunner, Ryan M.,Topczewski, Joseph J.
supporting information, p. 1604 - 1607 (2018/03/23)
A highly regioselective Wacker oxidation has been developed for the oxidation of cinnamyl azides. The catalytic oxidation tolerates the azide functionality, and more than 15 β-azido ketones were isolated (25-92% yield). High regioselectivity for the aryl ketone is observed in all cases. A robustness screen was conducted to determine functional group tolerance. The products of the oxidaiton can be readily diversified.
