Aziridinyl ketones and their cyclic anils. 8. 1,2-Diaryl-1,1a-dihydroazirino[1,2-a]quinoxalines from substitute o-phenylenediamines and chalcone dibromides
✍ Scribed by V. D. Orlov; N. P. Vorob'eva; N. N. Demenkova; V. S. Chesnovskii; F. G. Yaremenko
- Publisher
- Springer US
- Year
- 1988
- Tongue
- English
- Weight
- 393 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0009-3122
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✦ Synopsis
The reaction of 4-R-substituted (R = Br, CI, OC2H s, CmN, NO 2) 1,2-phenylenediamines with 1,3-diaryl-2,3-dibromo-l-propanones in the presence of triethylamine gave 1,2-diaryl-5-R-l,la-dihydroazirino[l,2-a]quinoxalines, which undergo isomerization in an acidic medium to give 2-aryl-3-arylmethylene-7-R-quinoxalines. The dipole moments were measured, and the polarities of the synthesized compounds are discussed.
The interestin the chemistry ofazirinoquinoxaline derivatives is due to the photochromism and thermochromisms that are characteristic for them and the high reactivities of the yields formed from them [i-6]. However, untillnow, only azirinoquinoxaiines based on 1,2-pheny~enediamine (I) have been described. In developing previous research [i, 5] we set out to study the products of the reaction of I and its 4-R-substituted compounds II-VI with 1,3-diaryl-2,3dibromo-l-propanones Vlla-g; the reaction was accomplished by refluxing the starting compounds in methanol f in the presence of triethylamine:
VIIIa-g; IXa~ Xa-g XIa-g; XIIa,c.g; XIIIa.g