1,2,3-Triazole and its derivatives. Development of methods for the formation of the triazole ring

Krivopalov, V. P.; Shkurko, O. P.

doi:10.1070/rc2005v074n04abeh000893

Cited by 208 publications

(105 citation statements)

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“…39 Um dos métodos gerais para a construção de anéis 1,2,3-triazólicos substituídos é a 1,5-eletrociclização intramolecular de compostos -diazocarbonílicos--substituídos. [40][41][42] Este método, também conhecido como eletrociclização do tipo [2N + 1N], consiste em combinar um reagente contendo dois átomos de nitrogênio com outro que possui apenas um átomo de nitrogênio, podendo se seguir duas vias distintas: a partir de cetonas ou ésteres -amino-,-insaturados, faz-se a reação de transferência de diazo (Via I) ou a partir de um composto -diazocarbonílico, forma-se, por sua reação com aminas, o intermediário -diazoimino (Via II). Nas duas vias, o intermediário -diazo--iminocarbonílico cicliza formando, então, os derivados de 1,2,3-triazóis (Esquema 8).…”

Section: Figura 3 Reagentes De Transferência De Diazounclassified

Ethyl 2-diazoacetoacetate (CAS No. 2009-97-4)

Lima¹

2016

Rev. Virtual Quim.

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This paper shows a brief abstract of the synthesis and applications of ethyl 2-diazoacetoacetate. This compound is considered an important reactant used as a synthetic precursor on various chemical transformations. The general method for their synthesis involves the direct diazo transfer reaction using different diazo group transfer reagent and basic conditions. Keywords: Ethyl 2-diazoacetoacetate; synthesis; applications. ResumoEste trabalho faz um breve resumo das sínteses e aplicações do 2-diazoacetoacetato de etila. Este composto é considerado um importante reagente utilizado como precursor sintético em diversas transformações químicas. O método geral para a sua preparação envolve a reação de transferência direta do grupo diazo, utilizando diferentes tipos de reagentes de diazotação sob condições básicas.Palavras-chave: 2-diazoacetoacetato de etila; síntese; aplicações.

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Section: Figura 3 Reagentes De Transferência De Diazounclassified

Ethyl 2-diazoacetoacetate (CAS No. 2009-97-4)

Lima¹

2016

Rev. Virtual Quim.

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“…Amongst many transformations, perhaps the most important one is the 1,3-dipolar cycloaddition reactions with alkynes to synthesize triazoles (Padwa, 1976). Triazoles are nitrogen heteroarenes, which have found a range of significant applications in pharmaceutical and agricultural industries (Krivopalov & Shkurko, 2005). On the other hand, the azide anion, N 3 -, is a versatile ligand because it shows a variety of coordination modes, e.g.…”

Section: S1 Commentmentioning

confidence: 99%

“…For general background to azide and triazole compounds, see: Dori & Ziolo (1973); Huynh et al (2003); Krivopalov & Shkurko (2005); Meyer et al (1998);Padwa (1976).…”

Section: Related Literaturementioning

confidence: 99%

Azido(benzonitrile-κN)[hydridotris(pyrazol-1-yl-κN²)borato](triphenylphosphine-κP)ruthenium(II)

Huang

Chen

et al. 2010

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 200 K; mean (C-C) = 0.006 Å; R factor = 0.041; wR factor = 0.093; data-to-parameter ratio = 13.6.Facile ligand substitution is observed when the rutheniumazide complex, [RuN 3 (Tp)(PPh 3 ) 2 ] [Tp,HB(pz) 3 , pz = pyrazolyl, PPh 3 = triphenylphosphine] is treated with benzonitrile, yielding the title compound, [Ru(C 9 H 10 BN 6 )(N 3 )(C 7 H 5 N)-(C 18 H 15 P)]. The asymmetric unit contains two crystallographically independent molecules. In each one, the Ru II atom is six-coordinated in a distorted octahedral geometry by five N atoms from an htpb ligand, an azide ligand and a benzonitrile ligand and one P atom from a triphenylphosphine (tpp) ligand. The azide group is almost linear and is coordinated to Ru with an average Ru-N-N angle of 124.9 (3) . Related literature

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“…Few methods are available for the selective preparation of N2-substituted-1,2,3-triazoles and they are limited to N2-hydroxymethyl-, 19 N2-allyl-, 21,21 or N2-aryl-1,2,3-triazoles. 22,23 We finally prepared and isolated the regioisomer N2-alkyl-1,2,3-triazoles by alkylation of NH-1,2,3-triazoles. N2-[N-(piperidin-1-yl)acetamide]-1,2,3-triazole derivatives are also reported here by comparison to rimonabant.…”

Section: Introductionmentioning

confidence: 99%

N-substituted-1,2,3-triazoles: synthesis, characterization and evaluation as cannabinoid ligands

Oliva¹,

Jagerovic²,

Goya³

et al. 2010

Arkivoc

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A series of new N1-, N2-and N3-substituted 1,2,3-triazole derivatives has been synthesized by cycloaddition of butyltin azide with substituted alkynes followed by a N-alkylation reaction. The regioisomers have been isolated and characterized using NMR techniques. GIAO/B3LYP calculations of the absolute shieldings have been performed to verify the assignments and so the structures have been unequivocally identified. The proportion in which the three isomers are obtained corresponds with the relative order of stability indicated by the energy values calculated at the B3LYP level. CB1 cannabinoid receptor binding assays have been performed but none of the compounds showed significant activity.

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1,2,3-Triazole and its derivatives. Development of methods for the formation of the triazole ring

Cited by 208 publications

References 335 publications

Ethyl 2-diazoacetoacetate (CAS No. 2009-97-4)

Ethyl 2-diazoacetoacetate (CAS No. 2009-97-4)

Azido(benzonitrile-κN)[hydridotris(pyrazol-1-yl-κN²)borato](triphenylphosphine-κP)ruthenium(II)

N-substituted-1,2,3-triazoles: synthesis, characterization and evaluation as cannabinoid ligands

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1,2,3-Triazole and its derivatives. Development of methods for the formation of the triazole ring

Cited by 208 publications

References 335 publications

Ethyl 2-diazoacetoacetate (CAS No. 2009-97-4)

Ethyl 2-diazoacetoacetate (CAS No. 2009-97-4)

Azido(benzonitrile-κN)[hydridotris(pyrazol-1-yl-κN2)borato](triphenylphosphine-κP)ruthenium(II)

N-substituted-1,2,3-triazoles: synthesis, characterization and evaluation as cannabinoid ligands

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Azido(benzonitrile-κN)[hydridotris(pyrazol-1-yl-κN²)borato](triphenylphosphine-κP)ruthenium(II)