78742-11-7Relevant articles and documents
Thermal Decomposition of 2-Amino-3-aziridino-1,4-naphthoquinones (1,2)
Antonini, Ippolito,Claudi, Francesco,Cristalli, Gloria,Grifantini, Mario,Martelli, Sante
, p. 399 - 404 (2007/10/02)
The course of the thermal decomposition of various 2-amino-3-substituted aziridino-1,4-naphthoquinones (Ia-g) was investigated.In all the cases, the thermal decomposition gave variable amounts of 2,3-diamino-1,4-naphthoquinone (II) and of substituted 1,2,3,4,5,10-hexahydrobenzoquinoxaline-5,10-diones (IIIa-g) with complete stereospecifity.The decomposition of the aziridines Ib,f also gave significative amounts of 2-amino-3-allylamino-1,4-naphthoquinones (IVb,f).In the case of 2-amino-3-(2'-phenyl-3'-ethylaziridino)-1,4-naphthoquinone (Ig), the formation of trans-1-phenyl-1-butene (V), 2-(1-phenylpropyl)-1H-napthoimidazole-4,9-dione (VI), 2-phenyl-3-ethyl-3,4,5,10-tetrahydrobenzoquinoxaline-5,10-dione (VII), 2-phenyl-3-ethyl-5,10-dihydrobenzoquinoxaline-5,10-dione (VIII), and a mixture of cis- and trans-4H-2,3,5,6-tetrahydro-2-phenyl-3-ethyl-5-iminonaphthooxazin-6-one (IX) also occured.Hypotheses concerning the mechanism and the steric course of this reaction are given.The reaction is a general method for the stereospecific synthesis of 2,3-disubstituted 1,2,3,4,5,10-hexahydrobenzoquinoxalines.
