2251-79-8Relevant academic research and scientific papers
Preparation and reactions of (1 H-tetrazol-5-yl)zinc pivalates
Tüllmann, Carl Phillip,Steiner, Sebastian,Knochel, Paul
, p. 2357 - 2363 (2020/08/19)
The preparation and reactivity of new solid heterocyclic organozinc reagents, namely N -protected (1 H -tetrazol-5-yl)zinc pivalates, as storable solids with appreciably air and moisture stability are reported. They are obtained in high yields from protected 1 H -tetrazoles by de-protonation using the mixed zinc-magnesium base TMPZnCl·Mg(OPiv) 2(abbreviated as TMPZnOPiv; TMP = 2,2,6,6-tetramethylpiperidyl). Subsequent cross-couplings and copper-catalyzed electrophilic aminations using hydroxylamine benzoates give access to functionalized 1 H -tetrazoles while tolerating many functional groups.
One-Pot Suzuki-Hydrogenolysis Protocol for the Modular Synthesis of 2,5-Diaryltetrazoles
Bertrand, Sophie,Jamieson, Craig,Livingstone, Keith
, p. 7413 - 7423 (2020/07/07)
2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the prac
Facile one-pot preparation of 5-aryltetrazoles and 3-arylisoxazoles from aryl bromides
Kobayashi, Eiji,Togo, Hideo
, p. 4226 - 4235 (2018/07/06)
The successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diphenylphosphoryl azide provided efficiently the corresponding 5-aryltetrazoles in good to moderate yields. Similarly, the successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diethyl acetylenedicarboxylate and Oxone provided efficiently the corresponding diethyl 3-arylisoxazole-4,5-dicarboxylates in good to moderate yields. Aromatic aldoximes are the key intermediates in both reactions, and 5-aryltetrazoles and 3-arylisoxazoles could be obtained from aryl bromides in one pot under transition-metal-free conditions.
Conversion of Arylboronic Acids to Tetrazoles Catalyzed by ONO Pincer-Type Palladium Complex
Vignesh, Arumugam,Bhuvanesh, Nattamai S. P.,Dharmaraj, Nallasamy
, p. 887 - 892 (2018/06/15)
A convenient synthesis of a library of tetrazoles through a novel and operationally simple protocol effecting the direct conversion of arylboronic acids catalyzed by a new ONO pincer-type Pd(II) complex under mild reaction conditions using the readily available reagents is reported. The palladium complex was reused up to four cycles in an open-flask condition.
Development and Demonstration of a Safer Protocol for the Synthesis of 5-Aryltetrazoles from Aryl Nitriles
Treitler, Daniel S.,Leung, Simon,Lindrud, Mark
, p. 460 - 467 (2017/03/24)
The search for a faster, safer protocol for the direct synthesis of 5-aryltetrazoles from aryl nitriles in the presence of sodium azide and an amine hydrochloride salt led to the discovery of a buffered system comprised of BnNH2, BnNH2·HCl, and NaN3. After optimization of reaction conditions and a thorough investigation of reaction safety, the procedure was demonstrated for the synthesis of several hundred grams of 4-chloro-2-(2H-tetrazol-5-yl)phenol. The generality of the developed reaction conditions was established by a small-scale reactivity screen using 16 additional aryl and heteroaryl nitrile substrates.
PHOTOSENSITIZERS, METHOD OF MAKING THEM AND THEIR USE IN PHOTOELECTRIC CONVERSION DEVICES
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Page/Page column, (2015/07/15)
Disclosed are novel photosensitizers, method of making them, and their use in photoelectric conversion devices such as the Dye Sensitized Solar Cell (DSSC). The photosensitizers have the Formula M(L1)2L2L3, M(L1)3L4 and ML4L5 where L
Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,3,4-Oxadiazoles using Chloroform as the Carbon Monoxide Source
Li, Zhengyi,Wang, Liang
supporting information, p. 3469 - 3473 (2016/01/25)
A palladium-catalyzed aminocarbonylation reaction of aryl halides with chloroform and tetrazoles has been developed, where chloroform was employed as the carbon monoxide (CO) source in the presence of cesium hydroxide. The in situ generated N-acylated tetrazoles were unstable and easily decomposed to afford 2,5-disubstituted 1,3,4-oxadiazoles. A wide range of tetrazoles and aryl halides reacted smoothly under the optimized reaction conditions to give the corresponding products in moderate to good yields.
Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation
Wang, Liang,Wu, Wenting,Chen, Qun,He, Mingyang
supporting information, p. 7923 - 7926 (2015/01/09)
Rh(III)-catalyzed direct olefination reaction via aromatic C-H bond activation is described using tetrazole as the directing group. This reaction provides a straightforward way for the synthesis of ortho-alkenyl aryl tetrazoles. Various functional groups tolerate the reaction conditions and afford the corresponding products in moderate to excellent yields.
Ligand-free nano copper oxide catalyzed cyanation of aryl halides and sequential one-pot synthesis of 5-substituted-1H-tetrazoles
Yapuri, Umanadh,Palle, Sadanandam,Gudaparthi, Omprakash,Narahari, Srinivasa Reddy,Rawat, Dhwajbahadur K.,Mukkanti, Khagga,Vantikommu, Jyothi
supporting information, p. 4732 - 4734 (2013/08/23)
An expedient and sequential one-pot synthesis of 5-substituted-1H- tetrazoles via [2+3] cycloaddition of aryl nitriles with sodium azide is reported. The required aryl nitriles were synthesized via the nano-copper oxide promoted cyanation of aryl iodides generated in situ.
One-step synthesis of 5-substituted 1 H -Tetrazoles from an aldehyde by reaction with acetohydroxamic acid and sodium azide under Bi(OTf)3 Catalysis
Sridhar, Madabhushi,Mallu, Kishore Kumar Reddy,Jillella, Raveendra,Godala, Kondalreddy,Beeram, Chinaramanaiah,Chinthala, Narsaiah
, p. 507 - 510 (2013/03/28)
An efficient one-step method for the synthesis of 5-substituted 1H-tetrazoles from aldehydes by reaction with acetohydroxamic acid and sodium azide using bismuth(III) triflate as the catalyst is described. Georg Thieme Verlag Stuttgart · New York.
