- 2-Pyrazinylnitrene and 4-pyrimidylnitrene. Ring expansion to 1,3,5-triazacyclohepta-1,2,4,6-tetraene and ring opening to (2-isocyanovinyl) carbodiimide
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Tetrazolo[1,5-a]pyrazine/2-azidopyrazine 9T/9A undergo photolysis in Ar matrix at cryogenic temperatures to yield 1,3,5-triazacyclohepta-1,2,4,6-tetraene 21 as the first observable intermediate, and 1-cyanoimidazole 11 and (2-isocyanovinyl)carbodiimide 22
- Addicott, Chris,Wong, Ming Wah,Wentrup, Curt
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- Synthesis of imidazole-activated ribonucleotides using cyanogen chloride
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We report the syntheses of ribonucleoside 5′-monophosphates activated with imidazole, using a mechanism which relies on the in situ generation of cyanogen chloride from the reaction of cyanide anion with hypochlorous acid. Cyanogen chloride reacts rapidly with imidazole to form diimidazole imine as the major product, a species which affords the activation of ribonucleoside 5′-monophosphates to their 5′-phosphorimidazolides.
- Yi, Ruiqin,Hongo, Yayoi,Fahrenbach, Albert C.
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supporting information
p. 511 - 514
(2018/01/19)
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- Alkoxy isothiocyanates, RO-N=C=S
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Methoxy isothiocyanate has been identified as a product of pyrolysis of the silver salt of N-methoxydithiocarbamic acid. It is also formed on FVT of 1-(N-methoxythiocarbamoyl)imidazole and 1-(N-methoxythiocarbamoyl)-1,2,4-triazole. Methoxy isothiocyanate was identified by IR spectroscopy in argon matrices at 10 K supported by good agreement with the ab initio and DFT calculated spectrum. Isopropoxy isothiocyanate was generated from the corresponding silver salt in a similar manner. The oligomerization of MeONCS to trithiolanes and tetrathianes is also described.
- Bech, Allan T.,Flammang, Robert,Pedersen, Carl Th.,Wong, Ming Wah,Wentrup, Curt
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p. 1869 - 1873
(2007/10/03)
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- Reaction of imidazoles with cyanogen bromide: Cyanation at N 1 or bromination at C 2?
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The reaction in acetonitrile solution of a number of imidazoles (1H-, 1-methyl-, 2-methyl-, 4-methyl-, 1,2-, 1,4- and 1,5-dimethyl-, 1-ethyl-, 1-benzyl- and 1-butyl-imidazole) and imidazole complexes ([Co(NH3)5(imH)](ClO4)3, [Co(NH3)5(im)] (ClO4)2 and [Co(NH3)5(1-Meim)] (ClO4)3) with BrCN has been studied. Those imidazoles bearing an N-alkyl substituent and having a hydrogen at C2 react to give the 2-bromo products, while the N-H imidazoles react to give W-cyano derivatives. The product(s) from the reaction of 1,2-dimethylimidazole with BrCN could not be characterized. Of the complexes, only [Co(NH3)5(im)] (ClO4)2 reacts, giving the 2-bromo product. Our observations suggest a lone pair on a ring nitrogen atom is necessary for an imidazole to react with BrCN, and a possible mechanism is suggested. The X-ray structure of 2-methylimidazole-1-carbonitrile is reported. Crystal data (-143°C) for C5H5N3: monoclinic, P21/c, a 10.201(5), b 7.110(3), c 7.227(3) A, β 100.47(2)°, V 515.4(4) A3, Z 4, dcalcd 1-380 g cm-3. Refinement of the structure converged with R1 0.0444 for 1183 reflections with Fo > 4F(Fo) and ωR2 0.1259 for all 1278 data.
- McCallum, Peter B.W.,Weavers, Rex T.,Grimmett, M. Ross,Blackman, Allan G.
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p. 159 - 165
(2007/10/03)
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- Synthesis of N-Cyanoazoles
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1-Cyanoimidazole, 1-cyano-2-methylimidazole, 1-cyanobenzimidazole, and 1-cyano-1,2,4-triazole were prepared by reaction of corresponding azoles with cyanogen bromide.Reactions of cyanogen bromide with sodium benzotriazolide and sodium pyridin-2-olate yield 1-cyanobenzotriazole and 2-cyanatopyridine.
- Purygin, P. P.,Pan'kov, S. V.
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p. 865 - 867
(2007/10/03)
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