- 40. Diazoaldehyde chemistry: Part 3. Synthesis of 4-acyl-1H-1,2,3-triazole derivatives
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Ten new α -diazo-β-oxoaldehydes were condensed with aniline, ammonia, hydroxylamine, and semicarbazide to yield new 4-acyl-(1-substituted)-1H-1,2,3-triazoles in moderate-to-good yields. The method is simple and regiospecific. The latter feature makes this method superior to the widely used acylacetylene + azide approach.
- Sezer, Oezkan,Dabak, Kadir,Akar, Ahmet,Anac, Olcay
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p. 449 - 453
(2007/10/03)
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- Diazoaldehyde Chemistry. Part 1. Transdiazotization of Acylacetaldehydes in Neutral-to-Acidic Medium. A Direct Approach to the Synthesis of α-Diazo-β-oxoaldehydes
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First ever non-deformylating transdiazotization of acylacetaldehydes was achieved: the reactions of 2-azido-1-ethylpyridinium tetrafluoroborate (4) with acylacetaldehydes 3 proceeded partially without deformylation to yield 16 new α-diazo-β-oxoaldehydes 1 along with diazomethyl ketones 2, especially in the presence of NaOAc (Scheme 1, Tables 1 and 2).The product distribution was substituent-dependent and could be correlated quantitatively.This new diazotization reaction appears as an alternative, direct, and more general method for the synthesis of these diazooxoaldehydes. α-Oxocycloalkanecarbaldehydes 5 gave only traces (if any) of α-diazocycloalkanones 7, and rearrangement products 6 were isolated (Scheme 2).Mechanisms of the reactions are discussed (Schemes 4 and 5).
- Sezer, Oezkan,Anac, Olcay
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p. 2323 - 2334
(2007/10/02)
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- TRANSFER OF THE DIAZO FUNCTION IN THE SERIES OF FLUORINATED 1,3-DIKETONES
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In the reaction of fluorinated 1,3-diketones with p-toluenesulfonyl azide under the conditions of diazo transfer hydrolytic elimination of the perfluoroacyl group occurs, and acyldiazomethanes are formed instead of the fluorine-containing diazo diketones.The reaction can be used for the synthesis of difficultly obtainable and labile 2-diazo ketones.
- Nikolaev, V. A.,Utkin, P. Yu.,Korobitsyna, I. K.
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p. 1059 - 1061
(2007/10/02)
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