Azidocarbonyl

A. N. Binnikov, A. S. Kulikov, N. N. Makhov, 1. V. Orchinnikov and T. S. Pivina, 4-Amino-3-azidocarbonyl Furoxan as an Universal Synthon for the Synthesis of Energetic Compounds of the Furoxan Series , 30th International Annual Conference of ICT, Karlsruhe, Germany, 1999, 58/1-58/10. 

Alkoxycarbonyl-l,2,4-oxadiazole allgemeine Arbeitsvorschrift108 Zur Losung von 46 mg (0,33 mmol) 3-Azidocarbonyl-l, 2,4-oxadiazol in 11 ml Xylol fiigt man 0,33 mol Alkohol und erhitzt 30 min zum Sieden. Nach dem Entfernen des Losungsmittels erhalt man die Produkte in praktisch quantitativer Ausbcute. 

Miller and co-workers, as part of their program in connection to the development of polypeptides as practical and readily modular chiral catalysts and new screening protocols for combinatorial synthesis, have been able to achieve efficient catalytic enantioselective conjugate additions of azides to acyclic enones [15]. As the example in Eq. (5) illustrates, the resulting 3-azidocarbonyls can be easily modified to afford N-containing heterocycles. 

Aminocarbonyl-5-phenyl- E8c, 567 [Ar-CO NH-NH-COCO-NH2 + (R3Si)2NH] 5-Formylamino-2-phenyl- E5, 988 (NH -> N-CHO) 2-(Hydroximino-methyl)-5-phenyl-E14b, 299 (CH2 - C = N-OH) Oxiran 3-Azidocarbonyl-2-phenyl-E5, 1205 (Cl -> N3)... 

Diamino-3-chloro-5-hydrazinocarbonylpyrazine with nitrous acid at 50-55° formed 2,6-diamino-3-azidocarbonyl-5-chloropyrazine, which, refluxed with a solution of guanidine hydrochloride and sodium isopropoxide in propan-2-ol, gave 2,6-diamino-3-chloro-5-guanidinocarbonylpyrazine and many similar preparations were reported (1371). 2-Amino-5-chloro-3-hydrazinocarbonylpyrazine treated with nitrous acid gave 2-amino-3-azidocarbonyl-5-chloropyrazine, which was pyrolyzed to 5-chloro-2-hydroxyimidazo(4,5-Z)]pyrazine (1226). 

The Curtius reaction of l-phenyl-3-azidocarbonyl-2-pyrazolin-5-one (320) in glacial acetic acid does not lead to the expected product (321), giving instead 2-acetyl-3-amino-l-phenyl-3-pyrazolin-5-one (322). A six-membered transition state involving the intermediate mixed anhydride (323) is proposed. 

Chromanones. An ethanolic soln. of 3-azidocarbonyl-2H-benzopyran refluxed 8 hrs., the ethanol evaporated, and the remaining urethan refluxed 5 hrs. with 10%-H2S04 chroman-3-one. Y 97%. R. Verhe and N. Schamp, Bull. Soc. chim. Belg. 82, 283 (1973). ... 

In contrast to diamino/urazan, diamino/uraxan is probably unstable. All attempts to generate it from rearrangements shown in Scheme 107 failed. However, Curtius rearrangement of 3,3 -bis(azidocarbonyl)-4,4 -azofuroxan 182 with subsequent isomerization afforded 4,4 -diamino-3,3 -azofuroxan 183 in 69% yield (Scheme 108) (98DOK499, 98MI2, 98MI6). 

Oxazoles (191) are producedwhen triphenylphosphine is treated simultaneously with an a-azidocarbonyl compound and an acyl halide. The intermediate iminophosphoranes (189) react with the acyl halide before they can react with themselves to give pyrazines. Elimination of phosphine oxide from the resulting salts may give the intermediate halo-genoimines (190), or the oxazoles may be formed via the betaines (192). 

Azidoacetyl chloride See other 2-azidocarbonyl compounds, organic acids... 

Acetyl azide, 0771 A-Azidocarbonylazepinc, 2728 Azidocarbonyl fluoride, 0339 Azidocarbonylguanidine, 0820 4-Azidocarbonyl-1,2,3-thiadiazole, 1069 Azidodithioformic acid, 0386 Benzene-l,3-bis(sulfonyl azide), 2210 Benzenesulfinyl azide, 2273 Benzenesulfonyl azide, 2274 Benzoyl azide, 2698... 

Bis(azidocarbonyl)cyclopropane, 1835 Bis(azidothiocarbonyl) disulfide, 1016 4-Bromobenzoyl azide, 2644... 

See also 2-azidocarbonyl compounds, cubanes, sulfinyl azides... 

Acetyl bromide, 0728 f Acetyl chloride, 0735 f Aciyloyl chloride, 1093 Azidocarbonyl fluoride, 0339 Benzenesulfinyl chloride, 2234 Benzenesulfonyl chloride, 2235 Benzoyl chloride, 2675 Benzyl chloroformate, 2931... 

ACYL AZIDES, 2-AZIDOCARBONYL COMPOUNDS, ORGANIC AZIDES... 

Certain 2-azidocarbonyl compounds and congeners have long been known as unstable substances [1]. Some members of a group of 2,5-dialkyl-3,6-diazido-1,4-benzoquinones decompose violently on melting [2], Individually indexed compounds are ... 

Barium Halocarbons, 0200 Barium peroxide, 0216 l,2-Bis(azidocarbonyl)cyclopropane, 1835 Calcium hypochlorite, 3924 Chromium trioxide Potassium hexacyanoferrate(3—), 4242 Diazidodimethylsilane, 0918... 

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