Rearrangements in heterocyclic synthesis. 2. Novel transformations of 2-aminonicotinonitrile and anthranilonitrile

…, U Siriwardane, NS Hosmane, SSC Chu

文献索引：Hosmane, Ramachandra S.; Lim, Benjamin B.; Summers, Michael F.; Siriwardane, Upali; Hosmane, Narayan S.; Chu, Shirley S. C. Journal of Organic Chemistry, 1988 , vol. 53, # 22 p. 5309 - 5315

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被引用次数: 36

摘要

5a or 6 in refluxing toluene-methanol, catalyzed by trifluoroacetic acid, yielded 2-amino-3-(l- methyl-1, 2, 4-triazol-3-y1) pyridine (8). A tentative mechanism for the conversion 5a-6-+ 8 has been proposed (Scheme IV). An alternative reaction pathway (Scheme V) was eliminated by the 15N labeling studies (Scheme VI). The translocative rearrangement of the vinylogous cyano hydrazidines of imidazole (la) and of pyrazole (lb) to the respective 3-(5- ...