Sodium azide, reaction with

In accordance with observations in halodinitrobenzene derivatives, fluoropyrazines are by far the most reactive of the halopyrazines. Fluoropyrazine undergoes facile reaction with sodium azide to give azidopyrazine (27), which exists in dynamic equilibrium with tetrazolo[l,5-a]pyrazine (28) (66JHC435). 

Reaction at position 4 of perfluotopyndme thus occurs readily with nitrogen nucleophiles, as exemplified by its reactions with sodium azide and with hydroxyl-amme [75, 76] (equation 39)... 

Butyl alcohol in synthesis of phenyl 1-butyl ether, 46, 89 1-Butyl azidoacetate, 46, 47 hydrogenation of, 46, 47 1-Butyl chloroacetate, reaction with sodium azide, 46, 47 lre l-4-i-BUTYLCYCLOHEXANOL, 47,16 4-(-Butylcyclohexanonc, reduction with lithium aluminum hydride and aluminum chloride, 47, 17 1-Butyl hypochlorite, reaction with cy-clohexylamine, 46,17 l-Butylthiourea, 46, 72... 

This reaction is catalyzed by the presence of divalent sulfur — e.g. sulfur ions, substances with S-S links, thioethers, thiazoles. If such substances are present in a chromatogram zone then the iodine applied with the reagent is consumed by reaction with sodium azide according to the above reaction. It is no longer available for the for-... 

Reaction with sodium azide even at —78°C leads to explosions attributed to fluorine azide formation. 

The stereoselective total synthesis of (+)-epiquinamide 301 has been achieved starting from the amino acid L-allysine ethylene acetal, which was converted into piperidine 298 by standard protocols. Allylation of 297 via an. V-acyliminium ion gave 298, which underwent RCM to provide 299 and the quinolizidine 300, with the wrong stereochemistry at the C-l stereocenter. This was corrected by mesylation of the alcohol, followed by Sn2 reaction with sodium azide to give 301, which, upon saponification of the methyl ester and decarboxylation through the Barton procedure followed by reduction and N-acylation, gave the desired natural product (Scheme 66) <20050L4005>. 

Dichlorooxadiazolo[3,4-3]pyrazine 181 forms the tricyclic tetrazole derivative 182 on reaction with sodium azide (Equation 44). The 7-azido group readily undergoes nucleophilic substitution <1997CHE977>. 

Pyranopyridines. The chlorobenzopyranoquinolone 325 reacts with hydrazides to give a triazole-fused ring system, such as in compound 326. Likewise, reaction with sodium azide gives the tetrazolo-fused product 327 (Scheme 79) <2003IJB2567>. 

Aryl and vinyl nitriles have been prepared very efficiently from the corresponding bromides by palladium-catalyzed reactions under microwaves. This energy source has been employed for the conversion of these nitriles into aryl and vinyl tetrazoles by cycloaddition reactions with sodium azide (Scheme 9.66). The direct transformation of aryl halides to the aryl tetrazoles in a one pot procedure could be accomplished both in solution and on a solid support [115], The reactions were complete in a few minutes, a reaction time considerably shorter than those previously reported for the thermal reactions. The cydoadditions were performed with sodium azide and ammonium chloride in DMF and, although no explosion occurred in the development of this work, the authors point out the necessity of taking adequate precautions against this eventuality. 

A" 0-Butenolide, 46, 22 /-Butyl alcohol, in synthesis of phenyl /-butyl ether, 45, 89 reaction with sodium cyanate and trifluoroacetic acid, 48, 32 /-Butyl azidoacctatc, 46, 47 hydrogenation of, 45, 47 /-Butyl carbamate, 48,32 /-Butyl chloroacetate, reaction with sodium azide, 45, 47 /ra S-4-/-BuTYI,CYCLOHEXANOL, 47,16... 

Boyer and Gunasekaren reported the synthesis of the furazan-based heterocycle NOTO (44), which contains 50 % by mass of nitrogen and is a liquid at room temperature. The flve-step synthesis of NOTO (44) starts from the diazotization of 4,4 -diamino-3,3 -azoxyfurazan (DAAF) (27), followed by reaction with sodium azide to form the diazide (42). Heating the diazide (42) as a solution in acetonitrile induces cyclization to the triazole (43) and this is followed by reduction and oxidation of the remaining azide group to complete the synthesis of NOTO (44). 

Pb(N03)2 + 2HF PbP2 + 2HNO3 Reaction with sodium azide yields lead azide ... 

The synthesis of inosamines from bromodeoxyinositols has been achieved by way of displacement reactions with sodium azide in boiling, aqueous 2-methoxyethanol or N,N-dimethylformamide.163... 

Alkyl (or aryl) 5-aminotetrazoles (38) can be prepared either from thioureas by reaction with sodium azide in the presence of lead carbonate89 or from 2-thiopseudourea hydriodides by reaction with sodium azide.70... 

Conversion of the 3, 5 -diacetyl thymidine 652 (R = Me) to the chloro derivative 653 followed by reaction with sodium azide in anhydrous DMF gave 654, whose hydrolysis gave 655 (86JHC1401). The 2 -deoxy-2, 2 -difluoro analog of 655 was prepared (93EUP576230) (Scheme 132). 

An interesting conversion of a 3-hydroxyflavanone (706) into a 3-aminoflavone (707) is effected by mesylation followed by reaction with sodium azide under mild conditions... 

Reaction of chalcone dibromides with sodium azide and subsequent treatment with base gives access to 3-aminoflavones (79LA174). The a-azido-2 -oxychalcones are also available from phenacyl bromides by reaction with sodium azide and then benzaldehyde. 

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