Abstract
Pivaloylpyruvic acid is an efficient reagent for preparative acylation of amines. A method for the synthesis of substituted pivaloylpyruvamides with domination of (Z)-β-keto-enol tautomer is proposed. The structure of pivaloylpyruvic acid and its amides, as well as the specific features of the reaction of pivaloylpyruvic acid with amines, are discussed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
B. C. Challis and J. A. Challis, inComprehensive Organic Chemistry, Eds. D. Barton and W. D. Ollis, Pergamon Press, New York, 1979,2.
J. March,Advanced Organic Chemistry. Reactions, Mechanisms and Structure, Wiley Interscience, 1985.
R. F. Saraeva, Ph. D. (Chem.) Thesis, Perm State Univ., Perm, 1973, 140 pp. (in Russian).
A. P. Kozlov, V. V. Ryabova, L. I. Varkentin, and Yu. S. Andreichikov,Khimiya nepredel'nykh soedinenii. Materialy Vsesoyuznoi konferentsii, posvyashchennoi pamyati A. M. Butlerova [The Chemistry of Unsaturated Compounds. Proc. All-Union Conf. in Memory of A. M. Butlerov], Kazan, 1986, part 2, 120 (in Russian).
A. P. Kozlov, V. V. Ryabova, and Yu. S. Andreichikov,Zh. Org. Khim., 1987,23, 1665 [J. Org. Chem. USSR, 1987,23 (Engl. Transl.)].
F. Couturier,C. R. Acad. Sci., 1910,150, 928.
A. Meister and J. P. Greenstein,J. Biol. Chem., 1948,175, 573.
O. V. Parfenov, S. A. Artem'ev, and V. Kh. Khamaev,Regional'noe soveshchanie respublik Srednei Azii i Kazokhstana po khimicheskim reaktivam [Regional Conf. of the Republics of Middle Asia and Kazakhstan on Chemicals], Tashkent, 1990,1, part 2, 292 (in Russian).
Yu. S. Andreichikov, Yu. A. Nalimova, S. P. Tendryakova, and Ya. M. Vilenchik,Zh. Org. Khim., 1978,14, 160 [J. Org. Chem. USSR, 1978,14 (Engl. Transl.)].
N. M. Igidov, E. N. Koz'minykh, A. V. Milyutin, E. S. Berezina, G. A. Shavkunova, I. B. Yakovlev, S. A. Shelenkova, V. E. Kolla, E. V. Voronina, and V. O. Koz'minykh,Khim. -Farm. Zh., 1996,30, No. 11, 21 [Pharm. Chem. J., 1996,30, No. 11 (Engl. Transl.)].
Yu. S. Andreichikov, A. V. Milyutin, I. V. Krylova, R. F. Saraeva, E. V. Dormidontova, L. P. Drovosekova, F. Ya. Nazmetdinov, and V. E. Kolla,Khim. -Farm. Zh., 1990,24, No. 7, 33 [Pharm. Chem. J., 1990,24, No. 7 (Engl. Transl.)].
E. N. Koz'minykh, D. Sc. (Pharm.) Thesis, Perm State Pharmaceutical Academy, Perm, 1999, 334 pp. (in Russian).
E. N. Koz'minykh, N. M. Igidov, and V. O. Koz'minykh,Vosem'desyat let farmatsevticheskomu obrazovaniyu i nauke na Urale: itogi i perspektivy. Materialy yubileinoi mezhvuzovskoi nauchno-prakticheskoi konferentsii, posvyashchennoi 275-letiyu Permi i 80-letiyu farmatsevticheskogo obrazovaniya na Urale [The Eightieth Anniversary of Pharmaceutical Education and Science in the Ural Region. Proc. Anniversary Scientific and Training Conf. of Schools of Higher Education, Dedicated to the 275th Anniversary of Perm and 80th Anniversary of Pharmaceutical Education in the Ural Region], Perm, 1998, 54 (in Russian).
O. Mumm and P. Bergell,Ber. Deutsch. Chem. Ges., 1912,45, 3046.
W. Küster and P. Schlack,Ber. Deutsch. Chem. Ges., 1924,57, 409.
W. Küster and E. Erfle,Ber. Deutsch. Chem. Ges., 1926,59, 1015.
Akiyoshi Ichiba, Sakae Emoto, and Masanobu Nagai,J. Sci. Res. Inst. (Tokyo), 1948,43, 23;Chem. Abstrs., 1949,43, 4673b.
E. Brömme and L. Claisen,Ber. Deutsch. Chem. Ges., 1888,21, 1131.
L. Claisen and N. Stylos,Ber. Deutsch. Chem. Ges., 1888,21, 1141.
K. Balenović, A. Deljac, B. Gašpert, and Z. Štefanac,Monatsh. Chem., 1967,98, 1344.
M. Poje and K. Balenović,J. Heterocycl. Chem., 1979,16, 417.
Author information
Authors and Affiliations
Additional information
Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1564–1568, September, 2000.
Rights and permissions
About this article
Cite this article
Koz'minykh, V.O., Igidov, N.M., Berezina, E.S. et al. Pivaloylpyruvic acid as a new acylating reagent for amines. Russ Chem Bull 49, 1552–1556 (2000). https://doi.org/10.1007/BF02495160
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02495160