Abstract
The advances in the synthesis of five-membered nitrogen-containing heterocycles by reactions involving 1,3-dipolar cycloaddition of conjugated and unconjugated nitroalkenes to various 1,3-dipoles (diazo compounds, azides, nitrile N-oxides, etc.) are systematized.
Similar content being viewed by others
Literature Cited
V. V. Perekalin, A. S. Sopova, and é. S. Lipina, Unsaturated Nitro Compounds [in Russian], Khimiya, Moscow (1982).
S. S. Novikov, G. A. Shvekhgeimer, V. V. Sevost'yanova, and V. A. Shlyapochnikov, The Chemistry of Aliphatic and Alicyclic Nitro Compounds [in Russian], Khimiya, Moscow (1974).
J. H. Boyer, Nitroazoles: The C-Nitro Derivatives of N- and N,O-Five-Membered Heterocycles, Vol. 1, edited by H. Feuer, VCH Publ., Deerfield Beach, Florida (1986).
J. Kochany, Wiadom. Chem., 32, 723 (1978).
R. S. Varma and G W. Kabalka, Heterocycles, 24, 2645 (1986).
S. Rajappa, Tetrahedron, 37, 1453 (1981).
V. V. Perekalin, Zh. Org. Khim., 21, 1171 (1985).
A. G. Barrett and G. Grabovski, Chem. Rev., 86, 751 (1986).
S. Rajappa and M. D. Nair, Advances in Heterocyclic Chemistry, Vol. 25, edited by A. R. Katritzky, Academic Press, Orlando (1979), p. 113.
M. Regitz and H. Heydt, 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, edited by A. Padwa, Wiley Intersci., New York (1984), p. 393.
W. E. Parham and J. L. Bleasdale, J. Am. Chem. Soc., 72, 3843 (1950).
W. E. Parham and J. L. Bleasdale, J. Am. Chem. Soc., 73, 4664 (1951).
G. Rembarz and B. Ernst, Z. Chem., 7, 421 (1967).
M. S. Malinovskii, A M. Korchagina, and N. M. Novikova, Scientific-Research Institute of Theoretical and Experimental Chemistry Deposited Paper No. 886, Cherkassy (1980); Ref. Zh. Khim., 7Zh58Dep (1981).
H. G. Viehe and R. Verbrüggen, Chimia, 29, 350 (1975).
R. K. Norris and T. A. Wright, Aust. J. Chem., 39, 281 (1986).
J. Kovac, A. Krutosiková, and E. Kada, Chémia, Heterocýklichych Zlucenin, Veda, Bratislava (1982), p. 190.
D. Ranganathan, C. B. Rao, S. Ranganathan, A. K. Mehrotra, and R. Jyengar, J. Org. Chem., 45, 1185 (1980).
K. Aimers and E. Cauer, Annalen, 470, 284 (1922).
K. Aumers and F. König, Annalen, 496, 252 (1932).
K. Aumers and V. Ungemach, Chem. Berg., 66, 1205 (1933).
W. E. Parham, C. Serres, and P. R. O'Connor, J. Am. Chem. Soc., 80, 588 (1958).
W. E. Parham, H. G. Braxton, and P. R. O'Connor, J. Org. Chem., 26, 1805 (1961).
W. E. Parham and W. R. Hasek, J. Am. Chem. Soc., 76, 799 (1954).
J. Van Alphen, Rec. Trav. Chim., 62, 491 (1943).
R. Huttel, K. Franke, H. Martin, and J. Riede, Chem. Ber., 93, 1435 (1960).
W. E. Parham, H. G. Braxton, and C. Serres, J. Org. Chem., 26, 1831 (1961).
A. Mustafa and A. H. E. Harhaash, J. Am. Chem. Soc., 76, 1383 (1954).
S. Ranganathan and C. S. Panda, Tetrahedron Lett., No. 41, 3841 (1971).
O. B. Kremleva, F. A. Gabitov, and A. L. Fridman, Summaries of Papers Presented at the 5th All-Union Conference on the Chemistry of Nitro Compounds [in Russian], Moscow (1974), p. 69.
F. A. Gabitov, A. L. Fridman, and O. B. Kremleva, Khim. Geterotsikl. Soedin., No. 11, 141 (1975).
O. B. Kremleva, F. A. Gabitov, and A. L. Fridman, Summaries of Papers Presented at the 6th All-Union Conference on the Chemistry of Nitro Compounds [in Russian], Moscow (1977), p. 13.
A. D. Shebaldova, L. M. Rizchenko, and M. L. Khidekel', Summaries of Papers Presented at the 6th All-Union Conference on the Chemistry of Nitro Compounds [in Russian], Moscow (1977), p. 69.
F. A. Gabitov, A. L. Fridman, and O. B. Kremleva, Zh. Org. Khim., 13, 1117 (1977).
A. L. Fridman, F. A. Gabitov, and V. D. Surkov, Zh. Org. Khim., 8, 2457 (1972).
F. A. Gabitov, A. L. Fridman, and A. D. Nikolaeva, Zh. Org. Khim., 5, 2245 (1969).
A. L. Fridman and F. A. Gabitov, USSR Author's Certificate No. 348570; Byull. Izobret., No. 25, 92 (19720.
A. L. Fridman, F. A. Gabitov, and A. D. Nikolaeva, Zh. Org. Khim., 7, 1309 (1971).
A. L. Fridman and F. A. Gabitov, USSR Author's Certificate No. 367097; Ref. Zh. Khim., 22N328 (1973).
O. P. Studzinskii and I. K. Korobitsina, Usp. Khim., 39, 1754 (1970).
T. J. De Boer and J. C. van Velzen, Rec. Trav. Chim., 78, 947 (1959).
T. J. De Boer, Tetrahedron. 20, Suppl. 1, 350 (1964).
J. Louwier-De Wal and T. J. De Boer, Rec. Trav. Chim., 87, 699 (1968).
J. C. van Velzen, C. Kruk, and T. J. De Boer, Rec. Trav. Chim., 90, 842 (1971).
J. L. Heinke, Chem. Ber., 31, 1395 (1898).
T. Severin and B. Bruck, Chem. Ber., 98, 4847 (1965).
T. Severin, B. Bruck, and P. Adhikary, Chem. Ber., 90, 3097 (1966).
R. Huisgen, R. Gresci, and J. Sawyer, The Chemistry of Alkenes [Russian translation], edited by S. Patai, Khimiya, Moscow (1969), p. 497.
M. P. Doyle, M. R. Colman, and R. L. Dorow, J. Heterocycl. Chem., 20, 943 (1983).
P. S. Engel, Chem. Rev., 80, 99 (1980).
P. C. Hiberty and Y. Jean, J. Am. Chem. Soc., 101, 2538 (1979).
J. S. Clovis, A. Eckell, R. Huisgen, R. Sustmann, G. Waallbillich, and V. Weberndörfer, Chem. Ber., 100, 1593 (1967).
Hong Soon-Yung and J. E. Baldwin, Tetrahedron, 24, 3784 (1968)
D. Pocar, S. Maiorana, and P. Dalla Croce, Gazz. Chim. Ital., 98, 949 (1968).
H. Dorn, Tetrahedron Lett., No. 24, 5123 (1985).
J. Stetinova, A. Jurasek, J. Kovac, M. Dandarova, and P. Safar, Coll. Czech. Chem. Commun., 51, 412 (1986).
G. Rembarz, B. Kirchhoff, and G. Dongowski, J. Prakt. Chem., 33, 199 (1966).
W. Lwowski, 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, edited by A. Padwa, Wiley Intersci., New York (1984), p. 559.
P. Callaghan and M. S. Gibson, Chem. Commun., No. 18, 918 (1967).
J. Bourgois, M. Bourgois, and F. Texier, Bull. Soc. Chim. France, II, Nos. 9–10, 485 (1978).
P. K. Kadaba, Tetrahedron. 25, 3053 (1969).
S. Maiorana, D. Pocar, and P. Dalla Croce, Tetrahedron Lett., No. 48. 6043 (1966).
D. Pocar, S. Maiorana, and P. Dalla Croce, Gazz. Chim. Ital., 98, 949 (1968).
N. Grassivaro, E. Rossi, and R. Stradi, Synthesis, No. 12, 1010 (1986).
P. Neuman, J. Heterocycl. Chem., 8, 51 (1971).
N. S. Zefirov and N. K. Chapovskaya, Vestnik Moskovsk. Gosudarstv. Univ. Ser 2. Khimiya, 9, 11 (1969).
N. S. Zefirov, N. K. Chapovskaya, and V. V. Kolesnikov, Chem. Commun., No. 17, 1001 (1971).
N. S. Zefirov, N. K. Chapovskaya, U. R. Apsalon, and V. V. Kolesnikov, Zh. Org. Khim., 8, 1335 (1972).
N. S. Zefirov, N. K. Chapovskaya, and U. R. Apsalon, Zh. Org. Khim., 12, 143 (1976).
G. Kh. Khisamutdinov, O. A. Bondarenko, and L. A. Kupryanova, Zh. Org. Khim., 11, 2445 (1975).
V. S. Velezheva, Yu. V. Erofeev, and N. N. Suvorov, Zh. Org. Khim., 16, 2157 (1980).
A. I. Sitkin, V. I. Klimenko, and G. Kh. Khisamutdinov, Ukr. Khim. Zh,., 45, 181 (1979).
Shin Chung-gi, Y. Yonezawa, and J. Yoshimura, Tetrahedron Lett., No. 1, 7 (1974).
H. U. Blank and J. J. Fox, J. Am. Chem. Soc., 90, 7175 (1968).
N. S. Issaks, Chem. Soc. Rev., 5, 181 (1976).
A. Padwa, K. F. Koehler, and A. Rodriguez, J. Am. Chem. Soc., 103, 4974 (1981).
A. Padwa, K. F. Koehler, and A. Rodriguez, J. Org. Chem., 49, 282 (1984).
J. Sims and K. N. Houk, J. Am. Chem. Soc., 95, 5798 (1979).
K. N. Houk, A. Bimanand, D. Mukherejee, J. Sims, Chang Yau-Min, D. C. Kafuman, and L. N. Domelsmith, Heterocycles, 7, 293 (1977).
A. Padwa, J. Fisera, K. F. Koehler, A. Rodriguez, and G. S. K. Wong, J. Org. Chem., 49, 276 (1980).
M. Joucla, D. Gree, and J. Hamelin, Tetrahedron, 29, 2315 (1973).
V. A. Tartakovskii, I. E. Chlenov, S. S. Smagin, and S. S. Novikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 583 (1964).
V. A. Tartakovskii, Doctoral Dissertation, Moscow (1966).
V. A. Tartakovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 165 (1984).
V. A. Tartakovskii, I. A. Sevost'yanova, and S. S. Novik, Zh. Org. Khim., 4, 240 (1968).
A. Barański, E. V. Arslanov, and G. A. Shvekhgeimer, Polish Chem. Soc. Meeting: Abstracts of Papers, Krakow (1980), p. 173.
A. Barański, Master's Dissertation, Moscow (1974).
G. A. Shvekhgeimer, A. Barański, and M. Grzegozek, Synthesis, No. 9, 611 (1976).
A. Barański and G. A Shvekhgeimer, Pol. J. Chem., 56, 459 (1982).
A. Barański and E. Cholewka, Studies in Organic Chemistry, Vol. 35, edited by J. Kovač and P. Zálupský, Elsevier, Amsterdam (1988), p. 217.
A. Barański, Pol. J. Chem., 56, 1585 (1982).
A. Barański, Polish Chemical Society Meeting: Abstracts of Papers, Krakow (1980), p. 174.
M. Von Muhlstadt and B. Schulze, J. Prakt. Chem., 56, 745 (1971).
A. Barański, Pol. J. Chem., 56, 257 (1982).
S. B. Bautz, N. F. Blom, J. C. A. Boeyens, and J. P. Michael, South Afr. J. Chem., 35, 166 (1982).
S. Rajappa, D. G. Advani, and R. Sreenivasan, Synthesis, No. 9, 656 (1974).
A. Padwa and J. G. MacDonald, Tetrahedron Lett., No. 32, 3218 (1982).
A. Padwa and J. G. MacDonald, J. Org. Chem., 48, 3189 (1983).
A. Barański, Pol. J. Chem., 60, 419 (1986).
P. Grunanger, Gazz. Chim. Ital., 84, 359 (1954).
P. Monforte and G. Lovecchio, Ann. Chim. (Roma), 46, 84 (1956).
K. Bast, M. Christi, R. Huisgen, and W. Mach, Chem. Ber., 106, 3258 (1973).
A. Barański, Pol. J. Chem., 60, 107 (1986).
A. Baranski, E. Cholewka, and T. Juska, Polish Chemical Society Meeting: Abstracts of Papers, Kielce (1984), p. 186.
A. Baranski and E. Cholewka, Abstracts of Papers Presented at the 6th International Conference on Organic Synthesis, Moscow (1986), p. A272.
A. Baranski and E. Cholewka, Pol. J. Chem., 62, 285 (1988).
A. Baranski and E. Cholewka, Pol. J. Chem., 63, 320 (1989).
G. A. Shvekhgeimer, V. I. Kelarev, V. I. Shvedov, and L. A. Dyankova, Zh. Vses. Khim. Obshch., 32, 461 (1987).
A. Baranski, Proceedings of the I. M. Gubkin Moscow Institute of the Petrochemical and Gas Industry. Petroleum and Gas and Their Products [in Russian], Moscow (1971), p. 172.
V. I. Kelarev, A. Baranski, and G. A Shvekhgeimer, Roczn. Chem., 47, 1669 (1973).
A. Baranski, G. A. Shvekhgeimer, and N. I. Kirillova, Pol. J. Chem., 54, 23 (1980).
A. Baranski and E. Cholewka, Polish Chemical Society Meeting: Abstracts of Papers, Poznan (1985), p. A6.
K. Harada, E. Kaji, and Sh. Zen, Chem. Pharm. Bull., 28, 3296 (1980).
J. F. W. Keana and G. M. Little, Heterocycles, 20, 1291 (1983).
G. A. Shvekhgeimer, V. I. Zvolinskii, and K. I. Kobrakov, Khim. Geterotsikl. Soedin., No. 4, 45 (1986).
D. R. Brittelli and G. A Boswell, J. Org. Chem., 46, 16 (1981).
A. Baranski, Pol. J. Chem., 55, 189 (1981).
A. Baranski, Pol. J. Chem., 58, 425 (1984).
A. Kozikowski, Acc. Chem. Res., 17, 4180 (1984).
R. D. Grant and I. T. Pinhey, Aust. J. Chem., 37, 1231 (1984).
L. A. Simonyan, N. P. Gambaryan, P. V. Petrovskii, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 370 (1968).
S. E. Denmark, M. S. Dappen, and C. J. Cramer, J. Am. Chem Soc., 108, 1306 (1986).
P. Nitti, G. Pitacco, V. Rinaldi, and E. Valentin, Croat. Chim. Acta. 59, 165 (1986).
G. Pitacco and E. Valentin, The Chemistry of the Functional Groups, Supplement F, Edited by S. Patai, Wiley Chichester-New York (1982), p. 623.
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 435–452, April, 1990.
Rights and permissions
About this article
Cite this article
Baranski, A., Kelarev, V.I. Synthesis of heterocycles by 1,3-dipolar cycloaddition reactions with the participation of nitroalkenes (review). Chem Heterocycl Compd 26, 371–386 (1990). https://doi.org/10.1007/BF00497204
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00497204