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Synthesis of mesityl-substituted 1,3,4-oxadiazoles from mesitotrichloride and aromatic and heteroaromatic acid hydrazides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

At interaction of 2,4,6-trimethylbenzotrichloride with aromatic (heteroaromatic) acid hydrazides in a mixture of 2,6-lutidine and tert-butanol the processes of alcoholysis and reductive condensation are suppressed. The corresponding 2-aryl- or 2-hetaryl-5-mesityl-1,3,4-oxadiazoles are obtained in high yields. The PMR, IR, and mass spectra of the products are studied.

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References

  1. I. S. Poddubnyi, L. I. Belen'kii, and M. M. Krayushkin,Khim. Geterotsikl. Soedin., No. 5, 686 (1994).

    Google Scholar 

  2. I. S. Poddubnyi, L. I. Belen'kii, and M. M. Krayushkin,Izv. Akad. Nauk, Ser. Khim., No. 5, 1246 (1996).

    Google Scholar 

  3. L. I. Belen'kii, I. S. Poddubnyi, and M. M. Krayushkin,Tetrahedron Lett.,36, 5075 (1995).

    Google Scholar 

  4. L. I. Belen'kii, I. S. Poddubnyi, and M. M. Krayushkin,Khim. Geterotsikl. Soedin., No. 6, 830 (1995).

    Google Scholar 

  5. I. F. Dvorko, N. Yu. Evtushenko, and V. N. Zhovtyak,Zh. Org. Khim.,57, 1157 (1987).

    CAS  Google Scholar 

  6. V. M. Feygelman, J. K. Walker, A. R. Katritzky, and Z. Dega-Szafran,Chem. Scripta,29, 241 (1989).

    CAS  Google Scholar 

  7. A. R. Katritzky (ed.),Physical Methods in Heterocyclic Chemistry, Academic, New York (1963).

    Google Scholar 

  8. R. A. Karakhanov, V. I. Kelarev, V. N. Koshelev, G. V. Morozova, and Ammar Dibi,Khim. Geterotsikl. Soedin., No. 2, 238 (1995).

    Google Scholar 

  9. H. Saihashi, N. Shimojo, and Y. Uehara,Chem. Pharm. Bull.,20, 1663 (1972).

    Google Scholar 

  10. L. I. Belen'kii, S. I. Luiksaar, I. S. Poddubnyi, and M. M. Krayushkin,Izv. Akad. Nauk, Ser. Khim., No. 11, 2309 (1998).

    Google Scholar 

  11. T. Nakano, V. E. Marquez, M. T. DiParsia, and C. Suarez,Org. Mass Spectrom.,13, 236 (1978).

    Article  CAS  Google Scholar 

  12. R. L. Ushakova, A. I. Mikaya, V. G. Zaikin, V. I. Kelarev, and G. A. Shvekhgeimer,Khim. Geterotsikl. Soedin., No. 4, 539 (1986).

    Google Scholar 

  13. A. Selva, F. Zerilli, B. Cavalleri, and G. G. Gallo,Org. Mass Spectrom.,9, 558 (1974).

    CAS  Google Scholar 

  14. S. Morrocchi, A. Ricca, A. Selva, and A. Zanarotti,Gazz. Chim. Ital.,99, 565 (1969).

    CAS  Google Scholar 

  15. M. J. Cook and E. J. Forbes,Tetrahedron,24, 4501 (1968).

    Article  CAS  Google Scholar 

  16. H. Meyer and J. Mally,Monatsh. Chem.,33, 400 (1912).

    Google Scholar 

  17. H. Hart and R. W. Fish,J. Am. Chem. Soc.,83, 4460 (1961).

    CAS  Google Scholar 

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Dedicated to Professor Henk van der Plas on his 70th birthday.

N. D. Zelinskii Institute of Organic Chemistry, Moscow 117913, Russia

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 557–563, April, 1999.

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Belen'kii, L.I., Luiksaar, S.I. & Krayushkin, M.M. Synthesis of mesityl-substituted 1,3,4-oxadiazoles from mesitotrichloride and aromatic and heteroaromatic acid hydrazides. Chem Heterocycl Compd 35, 492–498 (1999). https://doi.org/10.1007/BF02319340

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  • DOI: https://doi.org/10.1007/BF02319340

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