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6dimethylpyridine Heterocycle 59 57 69 65 43 40 Sec. B] 6 35 ADVANCES IN THE CHICHIBABIN REACTION MeKNH (92) (9') SCHEME 36 methylamide to give a 40% yield of 6-methylamino-4-phenylpyrimidine (91) (Scheme 36) (83RTC367). The fact that only the a-adduct on C-6 (92) was observed and 91 was the only product obtained indicated that the SN(ANR0RC) mechanism was not involved in the Chichibabin reaction when an alkyl amide was the nucleophile, even though the SN(ANR0RC) mechanism is operative when 29 reacts with potassium amide (Section II,B,2).
Much information on the existence and position of the a-adducts has been accumulated by 'H- and 13C-NMR spectroscopy (83AHC(33)95). The 1,5-naphthyridine isomer (180) readily formed 2-aminodihydro-1,5naphthyridinide (186) with potassium amide in liquid ammonia at -40°C Sec. VLD] 53 ADVANCES IN THE CHICHIBABIN REACTION NAPHTHYRIDI NES N \ 1,5(14 Nm N N Nm N / ' E N N ~ 1,6- 1,7- 1,8- 2,6- 2,l- 683 (182) (1 83) (184) (1 8 5) leaving no trace of 180 (78JOC1673; 81JOC2134). When the temperature was allowed to rise to + lWC, isomerization occurred to give 4-aminodihydro-1,5naphthyridinide (187) (Scheme 66).
The yield of both isomers was 72‘;/, which is about the same as obtained with sodium amide. The predominance of 89 is due most likely to steric hindrance caused by the bulkiness of the aminating agent. The situation is similar to the amination with sodium amide of 3-substituted pyridines at atmospheric pressure, in which the bulk of the 3-substituent directs the amount of 2-amino-5-isomer formed (Section IV), except that in this case, it is the size of the aminating group that decides the ratio of isomers.
Advances in Heterocycling Chemistry. Vol. 44 by Author Unknown