Synthesis of the novel naphtho-[1,2-e][1,2,4]triazolo[5,1-b][1,3]oxazine heterocyclic system
- 113 Downloads
Condensed 1,2,4-triazoles find use in human and veterinary medicine as tranquilizers [ 1], fungicides [ 2], antihistamine [ 3], and antihypertensive [ 4] preparations. In continuing our studies of the synthetic potential of naphthalene series o-quinone methides for the preparation of condensed azolo-1,3-oxazines [ 5] we have carried out a one-stage synthesis of the naphtho[1,2- e][1,2,4]triazolo[5,1- b][1,3]oxazines 2a,b from 3,5-dibromo-1,2,4-triazole and the Mannich base 1b or its quaternized analog 1a in the presence of K 2CO 3. We have also found that derivative 1a in refluxing acetonitrile in the absence of the potassium carbonate selectively formed 1-[(3,5-dibromo-1 H-1,2,4-triazol-1-yl)methyl]-2-naphthol ( 3).
Keywords3,5-dibromo-1,2,4-triazole o-quinone methides naphtho[1,2-e][1,2,4]triazolo[5,1-b][1,3]oxa- zines Mannich bases
- 1.M. Negwer, Organic Chemical Drugs and Their Synonyms, 6th edition, Akademie-Verlag, Berlin (1987).Google Scholar
- 2.C. J. Paget, US Pat. Appl. 3974286.Google Scholar
- 5.V. A. Osyanin, D. V. Osipov, and Yu. N. Klimochkin, Khim. Geterotsikl. Soedin., 136 (2011). [Chem. Heterocycl. Comp., 47, 108 (2011)].Google Scholar
© Springer Science+Business Media, Inc. 2012