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9:l. 23 ADVANCES IN THE CHICHIBABIN REACTION Sec. A] (57) (59 1 SCHEME19 The unusual reversal of isomers may be rationalized according to Scheme 19, where an equilibrium is proposed between the kinetically controlled anionic C-2 a-adduct 54 and the thermodynamically stable anionic C-6 a-adduct 55. Another equilibrium exists between the dianionic a-adducts 56 and 57. Support for the existence of dianionic a-adducts has been presented by Novikov et al. (76CHE210) and Kessar et al. (73IJC825). The function of the partial pressure of ammonia is to inhibit the formation of the dianionic a-adducts.
Some cine-substitution products (176 and 177) were also obtained (Scheme 65). From isotopic labeling studies, it was determined that the S,(ANRORC) mechanism was not involved. Pyrido[2,3-d] pyridazine (24) has been aminated in toluene with sodium amide at 60-70"C, giving a 52% yield of 2-aminopyrido[2,3-d]pyridazine (25) 52 CHARLES K. McGlLL AND ANGELA RAPPA [Sec. D (38% yield in liquid ammonia, see Section II,A,4) (69AJC1745). Pyrido[2,3b] pyrazine (178) formed a a-adduct upon treatment with potassium amide in liquid ammonia.
B] ADVANCES IN THE CHICHIBABIN REACTION 45 The amination of 1H-pyrrolo [2,3-f] isoquinoline (143)with excess sodium amide afforded 6-amino- 1H-pyrrolo[2,3-j'] isoquinoline (144)(Scheme 53) (84CHE399). The yield in xylene was 55% and in DMA it was 90%. The formation of 144 in liquid ammonia was observed by chromatography. Of the benzoquinolines, phenanthridine (14)was readily aminated in xylene or DMA to give 6-aminophenanthridine (15)(78RCR1042). Some derivatives of phenanthridine were aminated in xylene with sodium amide by Keene and Tissington (65JCS3032).