- Synthesis of 1,3-dioxacyclan-2-yl-substituted 1,2,3-triazoles
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A new method for preparing 4-(1,3-dioxacyclan-2-yl)-5-phenyl-1,2,3-triazoles in 30–75% yields has been developed on the basis of azide–alkyne cycloaddition to 2-phenylethinyl-1,3-dioxacyclanes. It has been shown that the best results are achieved when the reaction is carried out at 150–155°C in DMSO.
- Zlotskii,Raskil’dina,Golovanov,Bormotin,Bekin
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- Facile deallylation protocols for the preparation of N-unsubstituted triazoles and tetrazoles
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Two facile deallylation protocols have been developed for the preparation of N-unsubstituted triazoles and tetrazoles. The first protocol is a direct deallylation using a combination of a catalytic amount of nickel complex, NiCl2(dppe), and a stoichiometric amount of Grignard reagent, tBuMgCl. The second protocol is a stepwise deallylation through consecutive reactions of isomerization and ozonolysis. The isomerization from N-allylazoles to N-vinylazoles is catalyzed by a ruthenium complex, HRuCl(CO)(PPh3)3, and the following ozonolysis of the derived N-vinyl intermediates affords N-unsubstituted azoles. These protocols can be used complementarily depending on the type of functional groups in the parent allylated azoles.
- Kamijo, Shin,Huo, Zhibao,Jin, Tienan,Kanazawa, Chikashi,Yamamoto, Yoshinori
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p. 6389 - 6397
(2007/10/03)
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- CYCLOADDITION OF HYDRAZOIC ACID TO α,β-ACETYLENIC ALDIMINES
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The selectivity of the reaction of hydrazoic acid with α,β-acetylenic aldimines R1CCCH=NR2 was found to be independent of the nature of the substituents R1 and R2: in all the cases studied the addition occurs
- Piterskaya, Yu. L.,Khramchikhin, A. V.,Stadnichuk, M. D.
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p. 1614 - 1619
(2007/10/03)
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- REACTION OF ACETYLENE NITRILES WITH AZIDES
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The addition of organic and inorganic azides to 3-phenylpropynenitrile and 4-phenyl-2-hydroxy-3-butynenitrile was investigated.It was shown that organic azides add to 3-phenylpropynenitrile exclusively at the triple bond.The reaction with aluminum azide takes place with the participation of the acetylene bond and the nitrile group.The reaction of 4-phenyl-2-hydroxy-3-butynenitrile with azides is accompanied by decomposition to phenylpropargylaldehyde with the subsequent formation of 4-formyl-1,2,3-triazole.The oxidation of 4-phenyl-2-hydroxy-3-butynenitrile withactive manganese dioxide with the simultaneous addition of the azides leads to the formation of 4-carboxy-5-phenyl-1,2,3-triazole.
- Vereshchagin, L. I.,Filippova, T. M.,Bol'shedovorskaya, R. L.,Gavrilov, L. D.,Pavlova, G. A.
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p. 128 - 132
(2007/10/02)
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