Cyclization of Certain Heterocyclic Azides

Reynolds, G. A.; VanAllan, J. A.; Tinker, John F.

doi:10.1021/jo01091a010

Cited by 62 publications

(19 citation statements)

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“…29,30 The ex per i men tal re sults herein re veal that the char ac ter is tic IR fre quen cies 2160-2090 cm -1 ( N 3 ) agree with the azidoximes struc tures of these new com pounds 2. 29,30 The ex per i men tal re sults herein re veal that the char ac ter is tic IR fre quen cies 2160-2090 cm -1 ( N 3 ) agree with the azidoximes struc tures of these new com pounds 2.…”

Section: Re Sults and Discussionsupporting

confidence: 57%

Syntheses of 5‐(3‐Arylsydnon‐4‐yl)Tetrazole Derivatives

Shih

Lee

Yeh

2002

J Chinese Chemical Soc

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3‐Arylsydnone‐4‐carbohydroximic acid chlorides (1) could react with sodium azide to produce the corresponding 3‐arylsydnone‐4‐carbazidoximes (2), but not 1‐hydroxytetrazoles 3. Treatment of 3‐arylsydnone‐4‐carbazidoximes (2) with acid chlorides such as acetyl chloride (4a), propionyl chloride (4b) and benzoyl chloride (4c) in the presence of excess triethylamine generated the derivatives of the azidoximes 5. To obtain the desired tetrazoles, the azidoximes 2 should first cyclize directly with acetyl chloride (4a) or propionyl chloride (4b) to afford the acetyl or propionyl derivatives 6. The cyclized tetrazole derivatives 6 underwent deacylation upon heating in ethanol to give 1‐hydroxy‐5‐(3‐arylsydnon‐4‐yl)tetrazoles (3).

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Section: Re Sults and Discussionsupporting

confidence: 57%

Syntheses of 5‐(3‐Arylsydnon‐4‐yl)Tetrazole Derivatives

Shih

Lee

Yeh

2002

J Chinese Chemical Soc

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“…Les syntheses des composCs 1 a 4 ont Cte menCes selon les mtthodes decrites dans la litterature (24)(25)(26)(27)(28); l'azido-3 methyl-5 isoxazole 5 a t t t obtenu par action de l'azoture de sodium sur le sel de diaronium correspondant. La structure de ce compose a tte confirmke par spectrometrie de masse et par resonance magnttique nucl~aire du I3C (29).…”

Section: Introductionunclassified

Etude de l'équilibre dans les oxazolo[2,3-e], thiazolo[2,3-e] et isoxazolo[2,3-d]tétrazoles. II. Etude de l'effet de la température par dipolemetrie et résonance magnétique nucléaire

Faure¹,

Galy²,

Vincent³

et al. 1977

Can. J. Chem.

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The equilibrium constant in dioxane between azido and tétrazole isomers has been obtained for five heterocyclic azides (2-azido thiazoles, benzothiazole, benzoxazole, and 3-azido isoxazole) by proton nmr and dipole moment- studies. The last method involves a comparison between experimental and calculated (INDO, CNDO/2, CNDO/S) dipole moments. The CNDO/S method gives the best equilibrium constants and entropy factor (ΔS ∼ 50 J K−1 mol−1). A value of 114° for the C—N—N angle is found to account satisfactorily for certain properties (energy, dipole moment, photoelectron spectra) of aromatic azides. The heterocyclic azidoimines prefer the Z conformation.

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“…In view of the discrepancies in the literature regarding the structure of certain azides, a number of these compounds were synthesized [1]. In many cases, the azide group is adjacent to a ring nitrogen atom and cyclization to form the isomeric bicyclic tetrazole may take place as in the well known example of 1,2,3,3a-tetrazoaindene (III).…”

Section: Introductionmentioning

confidence: 99%

“…Nearly all of the examples of five-membered heterocyclic azides were recorded in the literature as being linear azides. Many compounds such as azidobenzimidazole and azidobenzoxazole, are true azides since they have a characteristic band in the infrared region of 2174 cm À1 ; others such as those obtained from 2-hydrazinobenzothiazole and from the corresponding selenazole, have cyclized structure [1]. It has been shown [3] that, azides have a strong distinct band at $2174 cm À1 in the infrared region, and a band at 280 nm in the ultraviolet.…”

Section: Introductionmentioning

confidence: 99%