- Preparation and reactions of (1 H-tetrazol-5-yl)zinc pivalates
-
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.
- Tüllmann, Carl Phillip,Steiner, Sebastian,Knochel, Paul
-
p. 2357 - 2363
(2020/08/19)
-
- One-Pot Suzuki-Hydrogenolysis Protocol for the Modular Synthesis of 2,5-Diaryltetrazoles
-
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
- Bertrand, Sophie,Jamieson, Craig,Livingstone, Keith
-
p. 7413 - 7423
(2020/07/07)
-
- Facile one-pot preparation of 5-aryltetrazoles and 3-arylisoxazoles from aryl bromides
-
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.
- Kobayashi, Eiji,Togo, Hideo
-
p. 4226 - 4235
(2018/07/06)
-
- Conversion of Arylboronic Acids to Tetrazoles Catalyzed by ONO Pincer-Type Palladium Complex
-
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.
- Vignesh, Arumugam,Bhuvanesh, Nattamai S. P.,Dharmaraj, Nallasamy
-
p. 887 - 892
(2018/06/15)
-
- Development and Demonstration of a Safer Protocol for the Synthesis of 5-Aryltetrazoles from Aryl Nitriles
-
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.
- Treitler, Daniel S.,Leung, Simon,Lindrud, Mark
-
p. 460 - 467
(2017/03/24)
-
- PHOTOSENSITIZERS, METHOD OF MAKING THEM AND THEIR USE IN PHOTOELECTRIC CONVERSION DEVICES
-
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
- -
-
Page/Page column
(2015/07/15)
-
- Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,3,4-Oxadiazoles using Chloroform as the Carbon Monoxide Source
-
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.
- Li, Zhengyi,Wang, Liang
-
supporting information
p. 3469 - 3473
(2016/01/25)
-
- Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation
-
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.
- Wang, Liang,Wu, Wenting,Chen, Qun,He, Mingyang
-
supporting information
p. 7923 - 7926
(2015/01/09)
-
- 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
-
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.
- Sridhar, Madabhushi,Mallu, Kishore Kumar Reddy,Jillella, Raveendra,Godala, Kondalreddy,Beeram, Chinaramanaiah,Chinthala, Narsaiah
-
p. 507 - 510
(2013/03/28)
-
- Ligand-free nano copper oxide catalyzed cyanation of aryl halides and sequential one-pot synthesis of 5-substituted-1H-tetrazoles
-
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.
- Yapuri, Umanadh,Palle, Sadanandam,Gudaparthi, Omprakash,Narahari, Srinivasa Reddy,Rawat, Dhwajbahadur K.,Mukkanti, Khagga,Vantikommu, Jyothi
-
supporting information
p. 4732 - 4734
(2013/08/23)
-
- Highly efficient synthesis of 5-substituted 1H-tetrazoles catalyzed by Cu-Zn alloy nanopowder, conversion into 1,5- and 2,5-disubstituted tetrazoles, and synthesis and NMR studies of new tetrazolium ionic liquids
-
A series of 5-substituted 1H-tetrazoles were synthesized through [3+2] cycloaddition reactions between nitriles RCN and NaN3 in the presence of Cu-Zn alloy nanopowder as catalyst. The 1,5-dibutyl, 1-butyl-5-hexyl, 2,5-dibutyl, and 2-butyl-5-hexyl derivatives were then used as building blocks to synthesize several novel tetrazolium ionic liquids (ILs) with EtSO 4-, OTf-, and NTf2- counterions. Whereas alkylation of the 2,5-dialkyltetrazoles selectively gave the N-4 alkylated onium salts, with the 1,5-dialkyl derivatives approximately 1:1 mixtures of two tetrazolium salts were formed by alkylation at N-3 and N-4. The triflate and ethyl sulfate salts are room-temperature ILs that are hydrophilic, whereas the NTf2 salts are low-melting ILs and are hydrophobic. The resulting tetrazolium-based ionic liquids were studied by various multinuclear and 2D NMR techniques including natural abundance 15N and 1H/15N correlations.
- Aridoss, Gopalakrishnan,Laali, Kenneth K.
-
experimental part
p. 6343 - 6355
(2011/12/03)
-
- One-pot synthesis of 5-substituted lH-tetrazoles from aryl bromides with potassium hexakis(cyano-κC)ferrate(4 -)(K4[Fe(CN)6]) as cyanide source
-
A one-pot procedure for the synthesis of 5-substituted 1H-tetrazoles through the three-component reaction between an aryl bromide, potassium hexakis(cyano-κC)ferrate(4 - ) (K4[Fe(CN)6]) and NaN3 catalyzed by [Pd(OAc)2
- Zhu, Yizhong,Ren, Yiming,Cai, Chun
-
experimental part
p. 171 - 175
(2009/05/30)
-
- Iron salts in the catalyzed synthesis of 5-substituted 1H-tetrazoles
-
A study was conducted to investigate the presence of iron salts in the catalyzed synthesis of 5-substituted 1H-tetrazoles. Para-trifluorotoluonitrile and trimethylsilyl azide were selected as model substrates for the initial metal source screening and the optimization of the reaction conditions. It was observed that the catalysis proceeded successfully producing tetrazole in 91% yield. A screening of various iron salts revealed that both the oxidation state of the iron and the counterion had a minor effect on the catalysis. Iron sources with different purity grades obtained from various providers were applied to investigate that the catalysis was not resulting from trace impurities in the metal salt. It was also observed that the catalysis proceeded successfully for a wide variety of aryl nitriles, providing tetrazoles in high yields. The best catalysis results were achieved with compounds that contained electron-withdrawing groups.
- Bonnamour, Julien,Bolm, Carsten
-
supporting information; experimental part
p. 4543 - 4545
(2009/12/27)
-