- 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
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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.
- Dighe, Satish N.,Jain, Kishor S.,Srinivasan, Kumar V.
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- Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1 H-tetrazol-5-amines
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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
- Nikolic, Andrea M.,Stanic, Jelena,Zlatar, Matija,Gruden, Maja,And?elkovic, Boban,Selakovic, Zivota,Ajdacic, Vladimir,Opsenica, Igor M.
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p. 4794 - 4803
(2021/04/06)
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- [3+1+1] type cyclization of ClCF2COONa for the assembly of imidazoles and tetrazolesvia in situgenerated isocyanides
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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.
- Song, Qiuling,Wang, Ya,Zhou, Yao
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supporting information
p. 6106 - 6109
(2020/06/10)
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- Novel two step synthesis of bis/Mono 1-aryl-1H-tetrazole-5-carboxylic acid
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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
- Chandrakumari, Sambandam,Sivakumar, Dhanavel,Manikandan, Haridoss,Gopalakrishnan, Mannuthusamy
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p. 1913 - 1925
(2019/05/15)
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- A stereocontrolled 1,2-addition reaction of tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines
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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
- Luo, Kai,Meng, Lingguo,Zhang, Yicheng,Zhang, Xiuli,Wang, Lei
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p. 765 - 780
(2013/04/10)
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- Chemistry of halonitroethenes, part 2: Trichloronitroethene as a building block for the novel synthesis of 5-chloro(nitro)methyl-substituted 1-aryltetrazoles
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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
- Zapol'Skii, Viktor A.,Yang, Xuena,Namyslo, Jan C.,Gjikaj, Mimoza,Kaufmann, Dieter E.
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p. 885 - 894
(2012/04/23)
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- 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]
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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.
- Aridoss, Gopalakrishnan,Laali, Kenneth K.
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experimental part
p. 2827 - 2835
(2011/06/23)
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- Indium triflate-catalyzed one-pot synthesis of 1-substituted-1H-1,2,3,4-tetrazoles under solvent-free conditions
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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
- Kundu, Dhiman,Majee, Adinath,Hajra, Alakananda
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experimental part
p. 2668 - 2670
(2009/08/09)
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