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

…, U Siriwardane, NS Hosmane, SSC Chu

Index: 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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Citation Number: 36

Abstract

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- ...