14210-81-2Relevant academic research and scientific papers
A novel synthesis of 1-aryl tetrazoles promoted by employing the synergy of the combined use of DMSO and an ionic liquid as the solvent system at ambient temperature
Dighe, Satish N.,Jain, Kishor S.,Srinivasan, Kumar V.
, p. 6139 - 6142 (2009)
The synergy of the combined use of DMSO and an ionic liquid viz. (bbim)+Br- has brought about a mild, convenient, efficient, and rapid protocol for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via the condensation of amines, triethyl orthoformate, and sodium azide at ambient temperature in excellent isolated yields (85-90%). The inherent Bronsted acidity of ionic liquid and high polarity of both IL and DMSO resulted in a significant enhancement in the reaction rate.
Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1 H-tetrazol-5-amines
Nikolic, Andrea M.,Stanic, Jelena,Zlatar, Matija,Gruden, Maja,And?elkovic, Boban,Selakovic, Zivota,Ajdacic, Vladimir,Opsenica, Igor M.
, p. 4794 - 4803 (2021/04/06)
The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely
[3+1+1] type cyclization of ClCF2COONa for the assembly of imidazoles and tetrazolesvia in situgenerated isocyanides
Song, Qiuling,Wang, Ya,Zhou, Yao
supporting information, p. 6106 - 6109 (2020/06/10)
A facile synthesis of imidazoles and tetrazolesvia[3+1+1] type cyclization of ClCF2COONa is developed. A diverse array of imidazoles and tetrazoles were obtained in decent yieldsviaisocyanide intermediates. Notably, this is the first example of the cycloaddition ofin situgenerated isocyanides.
Novel two step synthesis of bis/Mono 1-aryl-1H-tetrazole-5-carboxylic acid
Chandrakumari, Sambandam,Sivakumar, Dhanavel,Manikandan, Haridoss,Gopalakrishnan, Mannuthusamy
, p. 1913 - 1925 (2019/05/15)
Some novel compounds of bis/mono 1-aryl-1H-tetrazole-5-carboxylic acid are synthesized by the hydrolysis of two different synthesized esters, they are ethyl-1-aryl-1H-tetrazole-5-carboxylate and ethyloxo(1-aryl-1H-tetrazol-5-yl)acetate. The ethyl-1-aryl-1
A stereocontrolled 1,2-addition reaction of tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines
Luo, Kai,Meng, Lingguo,Zhang, Yicheng,Zhang, Xiuli,Wang, Lei
, p. 765 - 780 (2013/04/10)
A stereocontrolled 1,2-addition reaction of 1-aryl-1H-tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines was developed. In the presence of silver oxide (Ag2O), the 1,2-addition reaction generated (Z)-N-cyano enamines in good yields with exclusive formation of the Z-isomers. Meanwhile, the 1,2-addition reaction generated (E)-N-cyano enamines in the presence of Ag2O and potassium carbonate (K2CO 3) with high stereoselectivity and yields. Copyright
Chemistry of halonitroethenes, part 2: Trichloronitroethene as a building block for the novel synthesis of 5-chloro(nitro)methyl-substituted 1-aryltetrazoles
Zapol'Skii, Viktor A.,Yang, Xuena,Namyslo, Jan C.,Gjikaj, Mimoza,Kaufmann, Dieter E.
, p. 885 - 894 (2012/04/23)
Conversion of 1,1,2-trichloro-2-nitroethene with an excess of 1H-benzotriazole, followed by transamination of the resulting 1,1-bis(benzotriazol-1-yl)-2-chloro-2-nitroethene with different aniline derivatives provides the corresponding 1-(arylimino)-1-(be
Building heterocyclic systems with RC(OR)2+ carbocations in recyclable bronsted acidic ionic liquids: Facile synthesis of 1-substituted 1H-1,2,3,4-tetrazoles, benzazoles and other ring systems with CH(OEt)3 and EtC(OEt)3 in [EtNH 3][NO3] and [PMIM(SO3H)][OTf]
Aridoss, Gopalakrishnan,Laali, Kenneth K.
experimental part, p. 2827 - 2835 (2011/06/23)
1-Aryl/alkyl-1H-1,2,3,4-tetrazoles can conveniently be synthesized in one-pot reactions from the corresponding amines by reaction with TMSN 3 and CH(OEt)3 using the readily available, recyclable, Bronsted acidic ionic liquids [EtNH3][NO3] IL-1 and [PMIM(SO3H)][OTf] IL-2 under mild conditions in high yields. Based on comparative reactions, whereas both ILs are excellent promoters, reactions are completed with shorter reaction times and in higher yields with IL-2. Among 24 examples provided, identical products were obtained via the two ILs, except in the case of 2-aminobenzoic acid where tetrazole was formed with IL-2 and 2-ethylquinazolin-4(3H)-one was formed with IL-1. By leaving out TMS-N 3 from the reaction, the in-situ formed CH(OEt)2 + and EtC(OEt)2+ (via their corresponding orthoesters) react under sonication with o-phenylenediamine bearing various substituents, o-aminothiophenol and o-aminophenol to form a wide array of benzazoles (benzimidazole, benzothiazole and benzoxazole) and quinazolin-4(3H)-one in high yields (18 examples). The two ILs reacted differently in reaction with 2-aminobenzamide, whereas quinazolin-4(3H)one was formed with IL-2/CH(OEt)3, the "unexpected" N-ethylquinazolin-4(3H)one was isolated with IL-1/CH(OEt)3. The latter was also formed from 2-aminobenzoic acid in IL-1/CH(OEt)3. Mechanistic implications are addressed. The reported protocols enable rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and re-use of the ILs.
Indium triflate-catalyzed one-pot synthesis of 1-substituted-1H-1,2,3,4-tetrazoles under solvent-free conditions
Kundu, Dhiman,Majee, Adinath,Hajra, Alakananda
experimental part, p. 2668 - 2670 (2009/08/09)
A simple, efficient, and general method has been developed for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via a three-component condensation of amine, trimethyl orthoformate, and sodium azide in presence of a catalytic amount of indium triflate
