Abstract
Recent data on classical and modified methods for the synthesis of quinoline systems by the Skraup and Doebner-Miller reactions, not included in reviews on heterocycles, are discussed.
Similar content being viewed by others
References
R. G. Glushkov, I. B. Levshin, N. B. Marchenko, and E. N. Padeiskaya, Khim.-Farm. Zh., 18, 1048 (1984).
R. D. Chambers, D. Holling, G. Sandford, H. Puschmann, and J. A. K. Howard, J. Fluor. Chem., 117, 99 (2002).
A. Raadt, H. Griengl, M. Petsch, P. Plachota, N. Schoo, H. Weber, G. Brauneg, I. Kopper, M. Kreiner, and A. Zeiser, Tetrahedron: Asymmetry, 7, 473 (1996).
M. Z. Hoemann, G. Kumaravel, R. L. Xie, R. F. Rossi, S. Meyer, A. Sidhu, G. D. Cuny, and J. R. Hauske, Bioorg. Med. Chem. Lett., 10, 2675 (2000).
L. A. Kayukova and K. D. Pramyav, Khim.-Farm. Zh., 34, No. 1, 15 (2000).
R. C. Storr, P. M. O’Neill, and B. K. Park, Tetrahedron, 54, 4615 (1998).
S. Clavier, O. Rist, S. Hansen, L.-O. Gerlach, T. Hogberg, and J. Bergman, Org. Biomolec. Chem., 1, 4248 (2003).
V. L. Kovaleva, E. V. Shilova, and V. V. Poroikov, Khim.-Farm. Zh., 37, No. 6, 16 (2003).
Z. Skraup, Berichte, 13, 2086 (1880).
O. Doebner and W. M. Miller, Berichte, 16, 2464 (1883).
R. Elderfield (editor), Heterocyclic Compounds [Russian translation], Izd. Inostr. Lit., Moscow (1955), Vol. 4.
K. H. Park, H. S. Joo, K. I. Ahn, and K. Jun, Tetrahedron Lett., 36, 5943 (1995).
O. Schindler and W. Michaelis, Helv. Chim. Acta, 53, 776 (1970).
T. Gilchrist, Chemistry of Heterocyclic Compounds [Russian translation], Mir, Moscow (1996), p. 186.
A. Koppl and H. G. Alt, J. Mol. Catal., A: Chem., 154, 45 (2000).
H. Yamaguchi, Jpn. Patent 11322718; Chem. Abstr., 132, 11823 (2000).
R. H. F. Manske and M. Kulka, in: Organic Reactions [Russian translation], Vol. 7, Izd. Inostr. Lit., Moscow (1956), p. 100.
A. Surrey, in: Reference Book of Organic Reactions. Name Reactions in Organic Chemistry [Russian translation], Goskhimizdat, Moscow (1962), pp. 111, 231.
D. Barton and W. D. Ollis, Comprehensive Organic Chemistry [Russian translation], Vol. 8, Khimiya, Moscow (1985), p. 196.
B. I. Ardashev, Usp. Khim., 23, No. 4, 45 (1954).
I. I. Oleynik, J. Fluor. Chem., 91, 25 (1998).
H. Gershon, D. D. Clarke, J. J. McMahon, and M. Gershon, Monatsh. Chem., 133, 1325 (2002).
K. S. Sharma, S. Kumari, and R. P. Singh, Synthesis, 316 (1981).
J. D. Ringgenberg, T. K. Jones, and J. P. Edwards, Tetrahedron Lett., 39, 5139 (1998).
M. Buckley, N. Cooper, H. J. Dyke, F. P. Galleway, L. Gowers, A. F. Haughan, H. J. Kendall, C. Lowe, R. Maxey, J. G. Montana, R. Naylor, J. Oxford, J. C. Peake, C. L. Picken, K. A. Runcie, V. Sabin, A. Sharpe, and J. B. H. Warneck, Bioorg. Med. Chem. Lett., 12, 1613 (2002).
M. Bitlah, G. M. Buckley, N. Cooper, H. J. Dyke, R. Egan, A. Ganguly, L. Gowers, A. F. Haughan, H. J. Kendall, C. Lowe, M. Minnicozzi, J. G. Montana, J. Oxford, J. C. Peake, C. L. Picken, J. J. Piwinski, R. Naylor, V. Sabin, M.-Y. Shih, and J. B. H. Warneck, Bioorg. Med. Chem. Lett., 12, 1617 (2002).
I. N. Gracheva and A. I. Tochilkin, Khim. Geterotsikl. Soedin., 366 (1980).
D. D. Clarke, H. Gershon, and J. J. McMahon, Monatsh. Chem., 131, 795 (2000).
H. Gershon, D. D. Clarke, and M. Gershon, Monatsh. Chem., 133, 1437 (2002).
N. S. Prostakov, A. P. Krapivko, A. T. Soldatenkov, and N. D. Sergeeva, Khim. Geterotsikl. Soedin., 677 (1980).
V. V. Antonova, N. I. Kitaeva, A. M. Bespalova, and V. K. Pomonenkov, in: Basic Organic Synthesis and Petrochemistry [in Russian], Yaroslavl (1984), No. 20, p. 99.
P. Sanna, A. Carta, and G. Paglietti, Heterocycles, 53, 423 (2000).
Q. Han, H.-J. Lu, M.-C. Wang, and W.-Q. Shi, Zhengzhou Daxue Xuebao, Ziran Kexueban, 2, 80 (2000); Chem. Abstr., 134, 4842 (2001).
K. Kamienska-Trela, L. Kania, M. Bechcicka, and L. Kaczmarek, J. Mol. Struct., 661–662, 209 (2003).
M. H. Palmer, J. Chem. Soc., 3645 (1962).
J. Bourguignon, V. Lobregat, G. Queguiner, G. Dupas, P. Charpentier, and V. Levacher, Tetrahedron Lett., 39, 4013 (1998).
R. A. Blatchly and M. A. Greeley, Heterocycles, 29, 2345 (1989).
M. H. Lambourne, J. Chem. Soc., 119, 1294 (1922).
C. N. Carrigan, C. S. Esslinger, R. D. Bartlett, R. J. Bridges, and C. M. Thompson, Bioorg. Med. Chem. Lett., 9, 2607 (1999).
X.-G. Li, X. Cheng, J.-A. Ma, and Q.-L. Zhou, J. Organometal. Chem., 640, 65 (2001).
C. M. Leir, J. Org. Chem., 42, 911 (1977).
T. Morimitsu, Jpn. Patent 2000281651; Chem. Abstr., 133, 266742 (2000).
M. Matsugi, F. Tabusa, and J. Minamikawa, Tetrahedron Lett., 41, 8523 (2000).
X.-G. Li, X. Cheng, and Q.-L. Zhou, Synth. Commun., 32, 2477 (2002).
M. Palucki, D. L. Hughes, N. Yasuda, C. Yang, and P. J. Reider, Tetrahedron Lett., 42, 6811 (2001).
H. Z. Syeda Huma, R. Haider, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002).
Z. Wrobel, Tetrahedron, 54, 2607 (1998).
I. Ganesh and B. M. Reddy, J. Mol. Catal., A: Chem., 151, 289 (2000).
C. S. Cho, J. S. Kim, B. H. Oh, T.-J. Kim, S. C. Shim, and N. S. Yoon, Tetrahedron, 56, 7747 (2000).
R. R. Eva, US Patent 6103904; Chem. Abstr., 133, 165421 (2000).
Z. G. Song, M. Mertzman, and D. L. Hughu, J. Heterocycl. Chem., 30, 17 (1993).
G. Guanti, S. Perrozzi, and R. Riva, Tetrahedron: Asymmetry, 13, 2703 (2002).
S. Perrozzi, R. Riva, and G. I. Guanti, Tetrahedron: Asymmetry, 9, 3923 (1998).
M. R. Heinrich, W. Steglich, M. G. Banwell, and Y. Kashman, Tetrahedron, 59, 9239 (2003).
M. A. Bray, M. Gerspacher, A. von Sprecher, S. Kimmel, A. Beck, N. Subramanian, U. Niederhauser, G. P. Anderson, and H. Wiestner, Bioorg. Med. Chem. Lett., 8, 965 (1998).
M. R. Heinrich and W. Steglich, Tetrahedron, 59, 9231 (2003).
R. E. Armer, C. J. Dutton, S. D. W. Greenwood, J. Shaw, J. S. Barlow, D. H. J. Greenway, N. Lad, A. P. Thompson, K.-W. Thong, I. Tommasini, and N. Chopra, Bioorg. Med. Chem. Lett., 9, 2425 (1999).
Y. Qin, Chem. Reagents, 9, 115 (1987); Ref. Zh. Khim., 1Zh, 281 (1988).
H. Y. Choi, B. S. Lee, D. Y. Chi, and D. J. Kim, Heterocycles, 48, 2647 (1998).
Y. Ogata, A. Kawasaki, and S. Suyama, Tetrahedron, 25, 1361 (1969).
S. Yamada and H. Yamaguchi, Jpn. Patent 09157257; Chem. Abstr., 127, 34148 (1997).
A. Gopalsamy and P. V. Pallai, Tetrahedron Lett., 38, 907 (1997).
M.-E. Theoclitou and L. A. Robinson, Tetrahedron Lett., 43, 3907 (2002).
J. P. Edwards, T. K. Jones, J. D. Riggenberg, and E. M. Carreira, US Patent 6172241; Chem. Abstr., 134, 86171 (2001).
B. C. Ranu, U. Jana, and A. Hajra, Tetrahedron Lett., 41, 531 (2000).
W. R. Vaughan, Org. Synth., 3, 329 (1955).
M. A. Kerry, G. W. Boyd, S. P. Mackay, O. Meth-Cohn, and L. Platt, J. Chem. Soc, Perkin Trans. 1, 2315 (1999).
L. N. Lipunova, E. V. Nosov, G. A. Mokrushina, L. P. Sidorova, and V. N. Charushin, Khim.-Farm. Zh., 34, No. 1, 20 (2000).
K.-i. Saeki, M. Tomomitsu, Y. Kawazoe, K. Momota, and H. Kimoto, Chem. Pharm. Bull., 44, 2254 (1996).
P. Sanna, A. Carta, and G. Paglietti, Heterocycles, 50, 693 (1999).
K. Tanaka, Y. Kitahara, H. Suzuki, H. Osuga, and Y. Kawai, Tetrahedron Lett., 37, 5925 (1996).
N. B. Chapman, K. Clarke, and K. S. Sharraa, J. Chem. Soc. (C), 17, 2334 (1970).
B. Ermanno and M. D. Di, J. Heterocycl. Chem., 8, 693 (1971).
W. M. Owton, J. Chem. Soc., Perkin Trans. 1, 2409 (1999).
Z. Zhang, L. M. V. Tillekeratne, and R. A. Hudson, Synthesis, 377 (1996).
Z. P. Zhang, L. M. V. Tillekeratne, and R. A. Hudson, Tetrahedron Lett., 39, 5133 (1998).
Y. A. Jackson, M. A. Lyon, N. Townsend, K. Bellabe, and F. Soltanik, J. Chem. Soc., Perkin Trans. 1, 205 (2002).
J. Jones, Quinolines, Wiley-Interscience, London (1997), p. 11.
J.-C. Perch, G. Saint-Ruf, and N. P. Buu-Hoi, J. Chem. Soc. Perkin Trans. 1, 260 (1972).
P.-W. Phuan and M. C. Kozlowski, Tetrahedron Lett., 42, 3963 (2001).
T. Isao, H. Yoshuki, and H. Minoru, Chem. Pharm. Bull., 41, 747 (1993).
Y. Hamada and I. Takeuchi, Yakugaku Zasshi., 120, 206 (2000); Chem. Abstr., 132, 222393 (2000).
H. Fujiwara, Heterocycles, 45, 119 (1997).
H. Fujiwara and K. Kitagawa, Heterocycles, 53, 409 (2000).
N. P. Buu-Hoi, P. Jacquignon, D. C. Thang, and T. Bartnik, J. Chem. Soc. Perkin Trans. 1, 263 (1972).
S. V. Nekrasov and A. V. El’tsov, Zh. Org. Khim., 7, 188 (1971).
M. Dufour, N. P. Buu-Hoi, and P. Jacquignon, J. Chem. Soc. (C), 1415 (1967).
I. V. Borovlev and O. P. Demidov, Chem. Heterocycl. Comp., 39, 1417 (2003).
M. Dufour, N. P. Buu-Hoi, and P. Jacquignon, J. Chem. Soc. (C), 2070 (1968).
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 803–824, June, 2006.
Rights and permissions
About this article
Cite this article
Yamashkin, S.A., Oreshkina, E.A. Traditional and modern approaches to the synthesis of quinoline systems by the Skraup and Doebner-Miller methods. (Review). Chem Heterocycl Compd 42, 701–718 (2006). https://doi.org/10.1007/s10593-006-0150-y
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-006-0150-y