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The reactions of 2H-1,2,3-diazaarsoles with phenyl azide

✍ Scribed by Elena Ya. Zabotina; Igor A. Litvinov; Lyudmila G. Kuz'mina; Ruslan L. Korshunov


Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
595 KB
Volume
7
Category
Article
ISSN
1042-7163

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✦ Synopsis


2-

Phenyl-5-methyl-and 2,5-diphenyl-2 H-1,2,3-diazaarsoles la,b

react with phenyl azide to give several crystalline products: tricyclic derivatives 2a,b and 4,4'-bis(2H-l,2,3-diazaarsoles) 5a,b formed at room temperature, and a cycloadduct 6a obtained at + 4Β°C.

Compound 6a undergoes a fast rearrangement in solutions of Et,N or pyridine to give a stable dicoordinate arsenic compound, the 2H-1,2,3-diazaarsob 7a Heating solutions of 2a under reflux in an inert atmosphere leads to 5a and of 2b, in the presence of water, to 4b.

The structures of 2a, 4b, and 7a were characterized by X-rav crystal structure determinations.


πŸ“œ SIMILAR VOLUMES


ChemInform Abstract: Reactions of 2H-1,2
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Reactions of 2H-1,2,3-Diazaarsoles with Phenyl Azide. -The reaction of diazaarsoles such as (I) with phenyl azide provides tricyclic derivatives (cf. (III)), bis(diazaarsoles) (cf. (IV)), cycloadducts (cf. (V)) or theirefrom derived triazenodiazaarsoles (cf. (VI)) depending on the reaction condition

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## 5-Methyl-2-phenyl-2H-l,2,3-diazaarsole 1 reacts with ethyl diazoacetate to form a 1:I bicyclic product 3a, 8-ethoxycarbonyl-4-methyl-2-phenyl-l-ar.sa-2,3,6,7-tetraazabicyclo[3. ## 3. O]octa-3.7-diene. The latter isoinerizes to a two-coordinate arsenic compound 5, 3-ethoxycarbonyl-5-[a-(phenylh

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## Abstract By reaction with phenyl azide, 2‐cyano‐ and 2‐(ethoxycarbonyl)‐substituted cyclododecanones are converted into 5‐amino‐ and 5‐hydroxy‐1__H__‐1,2,3‐triazoles, respectively. The possible reaction mechanism is discussed.