Formyl‐ and Acyl‐1,2,3‐Triazoles

doi:10.1002/9780470187142.ch5

Chemistry of Heterocyclic Compounds: A Series of Monographs

1980

DOI: 10.1002/9780470187142.ch5

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Formyl‐ and Acyl‐1,2,3‐Triazoles

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1991

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Synthesis of 4‐Keto Substituted 1‐Alkyl‐1,2,3‐Triazoles from 5‐Substituted 1‐Phenyl‐l,2,3‐Triazole‐4‐Carbaldehydes

L'abbé

Essche

1991

Bulletin des Soc Chimique

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The triazoles 1 (mp 6ZoCl3 and 2 (mp llZ°C)4 were selected for our investigation. They were converted into the imines 3a-e and (a-e, and then heated in xylene at 130°C for 24 h.The resulting compounds 5a-e and 6a-e were hydrolyzed with silica gel and furnished the ketones 7a-e and 8s-e as the sole reaction products, which were characterized by spectral methods ( I R , N M R , MS) and microanalysis.122.6-126.2 (C-5 of 7 , 'JCH = 196 H z ) . 125.7-129.1 (C-5 of 8, , 1 9 2 . 6 -193.2 (CO of 7) and 185.5-185.9 (CO of 8). The imine precursors 3a-e and (a-e showed onebond 13CH=N coupling constants of 159-161 Hz indicating the E-configuration, a necessary prerequisite for rearrangement to occur.The sequence outlined above has two advantages over the classical method of 1,3-dipolar In the NMR spectra (CDC13) typical carbon resonances were found at bC 147.5-148.4 (C-4),

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Synthesis of 4‐Keto Substituted 1‐Alkyl‐1,2,3‐Triazoles from 5‐Substituted 1‐Phenyl‐l,2,3‐Triazole‐4‐Carbaldehydes

L'abbé

Essche

1991

Bulletin des Soc Chimique

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Formyl‐ and Acyl‐1,2,3‐Triazoles

Cited by 1 publication

References 75 publications

Synthesis of 4‐Keto Substituted 1‐Alkyl‐1,2,3‐Triazoles from 5‐Substituted 1‐Phenyl‐l,2,3‐Triazole‐4‐Carbaldehydes

Synthesis of 4‐Keto Substituted 1‐Alkyl‐1,2,3‐Triazoles from 5‐Substituted 1‐Phenyl‐l,2,3‐Triazole‐4‐Carbaldehydes

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