5-Methyl-2-phenyl-2H-1,2,3-diazaarsole in reaction with ethyl diazoacetate

✍ Scribed by Boris A. Arbuzov; Elena Ya. Zabotina; Evelina N. Dianova; Igor A. Litvinov; Victor A. Naumov; Shamil K. Latypov; Ahat V. Il'asov

• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: English
• Weight: 408 KB
• Volume: 3
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520030211

✦ Synopsis

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-(phenylhydrazono)ethyl]

1-1,2,4-diuzaarsole. The X-ray crystal structure analyses ofhoth products 3a and 5 have been carried out.

We have compared earlier 2H-1.2.3-diazaphospholes [ 1-51 and 2H-1.2.3-diazaarsoles in reactions with some disubsf ituted diazo-compounds (R2CN2, MePhCN,, Me2CN2). Monosubstituted diazo-compounds RCHN, were studied in reactions with diazaphospholes [6-81 but not with 2H-1.2.3.diazaarsoles. However, the 1H-1.2.4-diazaarsole reactivity with ethyl diazoacetate was described in Ref. [9]. We wish to report now on the reaction of 2H-1.2.3diazaarsole with ethyl diazoacetate.

S-Methyl-2-phenyl-2H-1.2.3-diazaarsole 1 and ethyl diazoacetate yield (Equation 1) two crystalline, yellow I : 1 products with mp 127-128 "C and 233-234 "C, respectively. The mass spectrum of the latter shows a molecular peak with 100%; intensity.