Synthesis of macroheterocyclic compounds on the basis of 3-chloro-2-hydrazinoquinoxaline
- 30 Downloads
2-Amino-1-[(3-chloro-2-quinoxalinyl)azo]naphthalene was obtained by oxidative coupling of 3-chloro-2-hydrazinoquinoxaline with 2-aminonaphthalenesulfonic acid; cross self-cyclization of the product was used to synthesize macrocyclic compounds, viz., [1,2,5,8,9,12]hexaazacyclotetradecene derivatives. 4-[(3-Chloro-2-quinoxalinyl)azo]-5-chloro-3-methyl-1-phenylpyrazole was obtained by the reaction of the 4-(3-chloro-2-quinoxalinyl)hydrazone of 2,4-dihydro-5-methyl-2-phenyl-3H-pyrazole-3,4-dione with POCl3. Reaction of this product with 2,2′-diaminoazobenzene under standard conditions gave [1,2,5,8,9,12]-hexaazacyclotetradecene derivatives.
KeywordsOrganic Chemistry Naphthalene Standard Condition Dione Hydrazone
Unable to display preview. Download preview PDF.
- 1.K. Sasse and G. Damagk, West German Patent No. 1104962; Chem. Abstr., 57, 8591 (1962).Google Scholar
- 2.W. Sauer, A. Scifert, and H. J. Binte, East German Patent No. 100965; Chem. Abstr., 82, 87649 (1975).Google Scholar
- 3.A. Könnecke and E. Lippman, Z. Chem., 18, 92 (1978).Google Scholar
- 4.B. A. Dreikorn, and T. D. Thibault, US Patent No. 4008322; Chem. Abstr., 86, 166387 (1977).Google Scholar
- 5.U. S. Tomsons, Candidate's Dissertation, Moscow (1976).Google Scholar
- 6.V. M. Dziomko and U. A. Tomsons, Reagents and Ultrapure Substances [in Russian], IREA, Moscow, No. 38 (1976), p. 208.Google Scholar
- 7.R. A. Karboni, J. C. Kauer, J. E. Castle, and H. E. Simmons, J. Am. Chem. Soc., 89, 2618 (1967).Google Scholar
- 8.V. M. Dziomko and M. N. Stopnikova, USSR Inventor's Certificate No. 670573; Byull. Izobret., No. 24, 79 (1979).Google Scholar
- 9.T. I. Balterham, NMR Spectra of Simple Heterocycles, Wiley-Interscience, New York-London (1973), p. 191.Google Scholar