Abstract
The condensation of hydrochloride sats of iminoesters of furan acids with hydrazides of carboxylic acids gives 2,5-disubstituted 1,3,4-oxadiazoles containing furan fragments. Such compounds are also formed in the condensation of hydrazides of 5-R-furan-2-carboxylic acids with hydrocloride salts of carboxylic acid iminoesters. The reaction of furan acids with hydrazine dihydrochloride in polyphosphoric acid gave symmetrically disubstituted 1,3,4-oxadiazoles containing furan fragments.
Similar content being viewed by others
References
R. A. Karakhanov, V. I. Kelarev, A. S. Remizov, Yu. N. Polivin, and D. Oiemaio, Khim. Geterotsikl. Soedin., No. 10, 1312 (1992).
R. A. Karakhanov, E. S. Bogacheva, I. Romero, and V. I. Kelarev, Khim. Geterotsikl. SOedin., No. 4, 449 (1991).
V. I. Kelarev, K. P. Kuatbekova, A. S. Remizov, R. A. Karakhanov, S. Sh. Gasanov, Yu. N. Polivin, and M. E. Panina, Abstracts of the Sixth Conference on Chemical Reagents [in Russian], Ufa, Baku (1993), p. 37.
V. I. Kelarev and G. A. Shvekhgeimer, Khim. Geterotsikl. Soedin., No. 3, 343 (1982).
A. A. Ponomarev and Z. V. Til', Zh. Obshch. Khim.,33, 2368 (1963).
W. R. Sherman, J. Org. Chem.26, 88 (1961).
L. D. Patsenker, A. P. Shkumat, N. V. Adonina, V. K. Polyakov, and V. F. Lavrushin, Ukr. Khim. Zh.,53, 628 (1987).
A. E. Obukhov, L. Sh. Afanasidi, L. D. Patsenker, and V. M. Shershukov, Khim Geterotsikl. Soedin., No. 10, 1414 (1989).
S. Patai (ed.), The Chemistry of Amidines and Imidates, John Wiley and Sons, London-New York (1975), p. 628.
G. S. Gol'din, M. V. Maksakova, V. G. Poddubnyi, and A. N. Kol'tsova, Zh. Obshch. Khim.,45, 2661 (1975).
E. P. Nesypov and A. P. Grekov, Usp. Khim. 38, 1184 (1964).
A. Hetzheim and K. Mockel, in: Advances in Heterocyclic Chemistry, Vol. 7 (1966), p. 183.
A. R. Katritzki (ed.), Physical Methods in Heterocyclic Chemistry [Russian translation], Mir, Moscow-Leningrad (1966), p. 539.
J. Imai, Makromol. Chem.83, 170 (1965).
É. Lukevits (eds.), Advances in Furan Chemistry Zinatne, Riga (1978), p. 19.
I. Hirao and Y. Kato, Bull. Chem. Soc. Jpn.,45, 2055 (1972).
T. Gracza, Z. Arnold, and Y. Kovacs, Coll. Czech. Chem. Commun.,51, 879 (1986).
Q. H. Porter and J. Baldes, Mass Spectrometry and Heterocyclic Compounds, Wiley Interscience, New York (1971).
H. Budzikewicz, C. Djerassi, and D. H. Williams, Mass Spectrometry of Organic Compounds, Holden-Day, San Francisco (1967), p. 615.
G. D. Krapivin, P. A. Pavlov, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 3, 403 (1987).
R. L. Ushakova, A. I. Mikaya, V. G. Zaikin, V. I. Kelarev, and G. A. Shvekhgeimer, Khim. Geterotsikl. Soedin., No. 4, 539 (1986).
T. Nakano, Y. E. Marques, M. T. Di Parsia, and C. Suarez, Org. Mass Spectr.,13, 236 (1978).
R. A. Khmel'nitskii, Khim. Geterotsikl. Soedin., No. 3, 291 (1974).
J. L. Cotter, J. Chem. Soc., No. 22, 5491 (1964).
R. A. Karakhanov, V. I. Kelarev, A. S. Kokosova, V. A. Malyshev, and V. I. Zav'yalov, Zh. Org. Khim.,28, 1750 (1992).
A. A. Ponomarev, Syntheses and Reactions of Furan Compounds [in Russian], Izd. Saratovsk. Gos. Univ., Saratov (1960).
H. L. Yalle, K. Losse, J. Martins, M. Holsing, F. M. Perry, and J. Bernstein, J. Am. Chem. Soc.,75, 1937 (1953).
V. I. Kelarev, S. Sh. Gasanov, R. A. Karakhanov, Yu. N. Polivin, K. P. Kuatbekova, and M. E. Panina, Zh. Org. Khim.,28, 2561 (1992).
P. Kupfer, M. Nagee, E. Wurthwein, and P. Allmann, Chem. Ber.,118, 3089 (1985).
H. Willey, J. Am. Chem. Soc.,76, 9935 (1954).
V. I. Kelarev and G. A. Shvekhgeimer, Khim. Geterotsikl. Soedin., No. 5, 645 (1980).
Additional information
Communication 3, see ref. [1].
I. M. Gubkin State Petroleum and Natural Gas Institute, 117917, Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 238–249, February, 1995. Original article submitted January 24, 1995.
Rights and permissions
About this article
Cite this article
Karakhanov, R.A., Kelarev, V.I., Koshelev, V.N. et al. Synthesis and properties of furan derivatives. 4. Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles containing furan fragments. Chem Heterocycl Compd 31, 208–218 (1995). https://doi.org/10.1007/BF01169682
Issue Date:
DOI: https://doi.org/10.1007/BF01169682