- An Expeditious Approach to Tetrazoles from Amides Utilizing Phosphorazidates
-
A novel method was developed for the synthesis of tetrazoles from amides utilizing diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate as both the activator of amide-oxygen for elimination and azide source. Various amides were converted into th
- Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
-
supporting information
p. 6244 - 6247
(2020/07/24)
-
- Iron (III)-porphyrin Complex FeTSPP as an efficient catalyst for synthesis of tetrazole derivatives via [2?+?3]cycloaddition reaction in aqueous medium
-
The metal complex (5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin-iron (III) chloride (FeTSPP) was new employed in an environmentally benign protocol as an efficient catalyst for a “click” chemistry approach for the synthesis of tetrazole and guanindinyltetrazole derivatives via [2?+?3] cycloaddition reaction of nitriles and azide derivatives in aqueous medium. The synthesized compounds were obtained in excellent yield, short reaction times and a recoverable catalyst.
- El-Remaily, Mahmoud Abd El Aleem Ali Ali,Elhady
-
-
- Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate
-
A novel method for the stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via the Beckmann rearrangement was developed using diphenyl phosphorazidate (DPPA) as both the oxime activator and azide source. Various ketoximes were transformed into the corresponding 1,5-disubstituted tetrazoles with exclusive trans-group migration and no E-Z isomerization of the ketoxime. This method enables the preparation of 1,5-disubstituted tetrazoles without using toxic or explosive azidation reagents.
- Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
-
p. 1295 - 1298
(2019/04/13)
-
- Transition-metal-free multinitrogenation of amides by C-C bond cleavage: A new approach to tetrazoles
-
A metal-free brand-new one-pot multinitrogenation of amides for the chemo- A nd regioselective synthesis of 1,5-disubstituted tetrazoles has been developed. By means of electrophilic amide activation, and further C-C bond cleavage and rearrangement, a diverse set of functionalized 1,5-DST derivatives were selectively constructed under mild conditions. As showcased in the mechanisms, the chemoselectivity is easily switched by the selection of the starting materials in the reaction.
- Li, Lian-Hua,Li, Ying-Xiu,Liang, Yong-Min,Niu, Zhi-Jie
-
supporting information
p. 11148 - 11151
(2020/04/22)
-
- Convergent Three-Component Tetrazole Synthesis
-
A microwave-accelerated, simple, and efficient method for the construction of the 1,5-tetrazole scaffold was developed. It comprises a multicomponent reaction of an amine, a carboxylic acid derivative, and an azide source. On the basis of the availability of the archetypical starting materials, this method provided very versatile synthetic access to 1,5-disubstituted tetrazoles. The usefulness of this method was demonstrated in the synthesis of biologically important fused tetrazole scaffolds and the marketed drug cilostazol.
- Chandgude, Ajay L.,D?mling, Alexander
-
p. 2383 - 2387
(2016/06/01)
-
- O -iodoxybenzoic acid mediated oxidative desulfurization initiated domino reactions for synthesis of azoles
-
A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.
- Chaudhari, Pramod S.,Pathare, Sagar P.,Akamanchi, Krishnacharaya G.
-
experimental part
p. 3716 - 3723
(2012/06/16)
-
- Synthesis of 1,5-disubstituted tetrazoles via Suzuki-Miyaura cross-coupling of 5-chloro-1-phenyltetrazole
-
Suzuki-Miyaura coupling reactions of 5-chloro-1-phenyl-tetrazole with various functionalized arylboronic acids were investigated. In the presence of catalytic amounts of SPhos/Pd(OAc)2 or RuPhos/Pd(OAc)2, the reaction proceeded smoot
- Tang, Qing,Gianatassio, Ryan
-
experimental part
p. 3473 - 3476
(2010/08/20)
-
- Direct C-H arylation and alkenylation of 1-substituted tetrazoles: Phosphine as stabilizing factor
-
(Chemical Equation Presented) Direct arylation and alkenylation of 1-substituted tetrazoles was achieved via Pd catalysis in the presence of CuI and Cs2CO3. Unlike the related reactions of imidazoles and purines, phosphine ligand was
- Spulak, Marcel,Lubojacky, Richard,Senel, Petr,Kunes, Jiri,Pour, Milan
-
experimental part
p. 241 - 244
(2010/04/06)
-
- Suzuki-Miyaura coupling reaction of aryl chlorides using di(2,6-dimethylmorpholino)phenylphosphine as ligand
-
Suzuki-Miyaura coupling was achieved on a variety of aryl chlorides by using di(2,6-dimethylmorpholino)phenylphosphine (L1) as a bulky electron-rich monoaryl phosphine ligand. We report the couplings of various chlorobenzenes and heteroaryl chlorides.
- Cho, Su-Dong,Kim, Ho-Kyun,Yim, Heung-seop,Kim, Mi-Ra,Lee, Jin-Kook,Kim, Jeum-Jong,Yoon, Yong-Jin
-
p. 1345 - 1352
(2007/10/03)
-
- Efficient synthesis of 1,5-disubstituted tetrazoles
-
A general method for the synthesis of 1,5-disubstituted tetrazoles from imidoylbenzotriazoles that involves mild reaction conditions and short reaction times. Georg Thieme Verlag Stuttgart.
- Katritzky, Alan R.,Cai, Chunming,Meher, Nabin K.
-
p. 1204 - 1208
(2008/02/02)
-
- A rationally designed universal catalyst for Suzuki-Miyaura coupling processes
-
Unprecedented scope, reactivity, and stability are displayed by a new catalyst system. This was demonstrated with general and efficient syntheses of sterically hindered (hetero)biaryls (see examples shown), mild coupling reactions of alkyl boron derivatives, and rapid coupling reactions of aryl chlorides at room temperature.
- Walker, Shawn D.,Barder, Timothy E.,Martinelli, Joseph R.,Buchwald, Stephen L.
-
p. 1871 - 1876
(2007/10/03)
-
- Palladium- and copper-catalyzed selective arylation of 5-aryltetrazoles by diaryliodonium salts
-
Palladium(0)-catalyzed arylation of 5-aryltetrazoles in t-BuOH at 80°C with diaryliodonium salts proceeds in the presence of copper(II) phenylcyclopropyl carboxylate regioselectively at the N2 position.
- Beletskaya, Irina P.,Davydov, Dmitri V.,Gorovoy, Matvey S.
-
p. 6221 - 6223
(2007/10/03)
-
- Preparation of 1,5-disubstituted tetrazoles under phase-transfer conditions
-
Imidoyl chlorides, obtained by common methods from a wide range of aromatic mono- and diamides, are smoothly converted to the corresponding tetrazoles in high yields by treatment with NaN3 under phase-transfer conditions.
- Artamonova,Zhivich,Dubinskii,Koldobskii
-
p. 1428 - 1430
(2007/10/03)
-
- A facile and convenient synthesis of substituted tetrazole derivatives from ketones or α,β-unsaturated ketones.
-
Triazidochlorosilane (SiCl4-NaN3 in situ) is a new and efficient reagent for the direct conversion of ketones or α,β-unsaturated ketones to the corresponding tetrazole derivatives in nearly quantitative yield.
- El-Ahl, Abdel-Aziz S.,Elmorsy, Saad S.,Soliman, Hanan,Amer, Fathy A.
-
p. 7337 - 7340
(2007/10/02)
-
- Improved Schmidt synthesis of 1,5-disubstituted 1H-tetrazoles from ketones
-
On treatment with an excess of sodium azide in the presence of titanium(IV) chloride in boiling acetonitrile, both aliphatic and aromatic ketones are smoothly converted to 1,5-disubstituted 1H-tetrazoles in high yields.
- Suzuki,Hwang,Nakaya,Matano
-
p. 1218 - 1220
(2007/10/02)
-
- TETRAZOLES. XXVIII PREPARATION AND PROPERTIES OF 2,3-DIPHENYL-5-ALKYLTETRAZOLIUM SALTS
-
The oxidation of 1,5-diphenyl-3-alkylformazanes by potassium permanganate in methylene chloride (chloroform)-water two-phase systems is a convenient method for the preparation of 2,3-diphenyl-5-alkyltetrazolium salts.The 2,3-diphenyl-5-alkyltetrazolium salts can be used as catalysts for interphase transfer in reactions proceeding in organic solvent-water two-phase systems, with a neutral or acid aqueous phase.The catalytic activity of 2,3-diphenyl-5-alkyltetrazolium salts increases with increase in the length of the alkyl substituent in the 5-position of the tetrazole ring.
- Nikonova, I. V.,Koldobskii, G. I.,Zhivich, A. B.,Ostrovskii, V. A.
-
p. 1951 - 1957
(2007/10/02)
-
- Intramolecular Reaction Between Nitro and Carbodi-imide Groups; A New Synthesis of 2-Arylbenzotriazoles
-
1-(2-Nitrophenyl)-5-phenyltetrazole (5b) decomposes when heated to give nitrogen, carbon dioxide, and 2-phenylbenzotriazole (6) in high yield.This new molecular rearrangement proceeds via 2-nitrophenyl(phenyl)carbodi-imide (8).Other precursors of this carbodi-imide, i.e. oxadiazolone (10), oxadiazolethione (11), oxathiadiazole 2-oxide (12), and the aminimide (16), and carbodi-imide itself, all give 2-phenylbenzotriazole (6) on thermolysis, the last three in high yield.This reaction is general for diarylcarbodi-imides with an ortho nitro group, and their precursors, and it provides a useful new route to 2-arylbenzotriazoles.A sequence of electrocyclic ring closing and opening reactions (Scheme 5) is proposed as the mechanism of this process.The key intermediate, 2-phenyl-1,2,4-benzotriazin-3-one 1-oxide (19) has been isolated from a careful thermolysis of (12) in toluene; in solution it is in reversible equlibrium with the ring-opened form (20).This new nitro-carbodi-imide group interaction has been extended to the more stable nitrobiphenyl(phenyl)carbodi-imide (25) and nitronaphthyl(phenyl)carbodi-imide (24) which, on flash vacuum pyrolysis, give benzimidazophenanthridine (29) and benzindazole 1-oxide (32) respectively, in new rearrangements.
- Houghton, Peter G.,Pipe, David F.,Rees, Charles W.
-
p. 1471 - 1480
(2007/10/02)
-