Synthesis of 5‐Diazomethyl Substituted V‐Triazolo [4,5‐D] Pyrimidines

We have recently reported that condensation of 5-azido-4-cyano-1-substituted 1,2,3-triazoles with active methylene nitriles in the presence of a strong base yields bis [l,2,3] The structure of the diazo form 2 was established unambiguously by spectral methods (IR, ' H and 13C NMR), whereas the ring-closed form was assumed to have the angular structure 1 rather than the linear structure 3 which has an unfavourable ortho-quinoid arrangement. The angular structure was also postulated by Tennant' and Westerlund3 for similar systems. the benzyl methylene proton absorptions at 6 6.33, 5.80 and 5.95 respectively. The low field absorption at 6 6.33 is attributed to structure 4 where there is a deshielding effect of a substituent in the peri coupled with an anisotropic effect of the triazole ring.The deshielding effect of the peri-substituent is also observed in the 13C NMR spectrum with a CH2 absorption at 6 54.1 for 5 and 51.1 for 5. tion of 6 (6 9.88) is deshielded with respect to that of 5 (6 9.3), whereas 5 absorbs at 6 This is deduced from the 'H NMR spectra by integration of A s expected, the ring proton at the 4-posi-9.35.6-679 -

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On the Equilibrium Position of Bis[1,2,3] Triazolopyrimidines (A revision)

L'abbé

Godts

Toppet

1986

Bulletin des Soc Chimique

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Synthesis and Thermal Decomposition of 4‐Azidoisoxazoles

L'abbé

Godts

1987

Bulletin des Soc Chimique

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ABSTRACT.give a-cyanodiazoketones 2 . L and, in the case of fi, also the N- We will also discuss the mechanism of decomposition of REACTION PRODUCTS When the aminoisoxazoles &,b were diazotized with sodium nitrite in hydrochloric acid at 0 -5OC, and then treated with sodium azide, the expected azidoisoxazoles 2 , p were obtained in only small amounts (ranging from 0 to 8 % ) .The major products of the reactions were found to be the a-cyanodiazoketones -3a,b and, in the case of 2, also the N-hydroxytriazole 1.In order to optimize the yields of &,a the reaction conditions were varied, including a change of solvent, nitrosation reagent and temperature. The best results were obtained when the diazotization was carried out at a temperature between -15 and -lO°C, yielding 30% of &,k under the conditions described in the Experimental Section (Method B).-229 -

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Synthesis and Crystal Structure of Bis [1,2,3] Triazolo [1,5‐a:4′,5′‐d] Pyrimidin‐9‐Ones

L'abbé

Godts

Toppet

et al. 1987

Bulletin des Soc Chimique

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Synthesis of 5‐Diazomethyl Substituted V‐Triazolo [4,5‐D] Pyrimidines

Cited by 14 publications

References 11 publications

On the Equilibrium Position of Bis[1,2,3] Triazolopyrimidines (A revision)

On the Equilibrium Position of Bis[1,2,3] Triazolopyrimidines (A revision)

Synthesis and Thermal Decomposition of 4‐Azidoisoxazoles

Synthesis and Crystal Structure of Bis [1,2,3] Triazolo [1,5‐a:4′,5′‐d] Pyrimidin‐9‐Ones

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