Abstract
Published data on the synthesis and reactions of indolopyridines with one bridgehead heteroatom and their benzannelated derivatives are reviewed for the first time.
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REFERENCES
S. A. Zaitsev andR. G. Glushkov, Khim.-Farm. Zh., No. 5, 9 (1990).
J. Ewing,G. K. Hughes,E. Ritchie, andW. C. Taylor, Aust. J. Chem., 6, 78 (1953).
O. S. Radchenko,V. L. Novikov, andG. B. Elyakov, Tetrahedron Lett., 38, 5339 (1997).
D. D. Chapman, Res. Disl, 35 (1974); Chem. Abstr.,83, 81014 (1975).
K. B. Soroka andJ. A. Soroka, Tetrahedron Lett., 21, 4631 (1980).
T. Kotowski,A. Orzeszko,W. Skubiszak,T. Stacewicz, andJ. A. Soroka, Opt. Appl., 14, 267 (1984).
T. Kotowski,W. Skubiszak,T. Stacewicz,J. A. Soroka, andK. B. Soroka, Opt. Appl., 18, 153 (1988).
W. Verboom,E. O. M. Orlemans,H. J. Berga.M. W. Schetinga, andD. N. Reinhoudt, Tetrahedron, 42, 5053 (1986).
A. Kh. A. Rodriges, Thesis for Candidate of Chemical Sciences [in Russian], Moscow (1991).
M. Goldbrunner,G. Loidl,T. Polossek,A. Mannschreck, andE. Angerer, J. Med. Chem., 40, 3524 (1997).
T. L. Gilchrist,P. D. Kemmit, andA. L. Germain, Tetrahedron, 53, 4447 (1997).
P. S. Sunkara,T. L Bowlin,P. S. Liu, andA. Sjoerdsma, Biochem. Biophys. Res. Commun., 148, 206 (1987).
J. R. Winkler andH. L. Segal, J. Biol. Chem., 259, 1958 (1984).
K. B. Soroka andJ. A. Soroka, Chemica Scripta, 29, 167 (1989).
A. L. Germain,T. L. Gilchrist, andP. D. Kemmitt, Heterocycles, 37, 697 (1994).
N. Takeuchi,M. Tanabe,M. Hagiwara,K. Goto,T. Koike, andS. Tobinaga, Heterocycles, 38, 613 (1995).
D. D. Chapman,J. K. Elwood,D. W. Heseltine,H. M. Hess, andD. W. Kurts, J. Chem. Soc. Chem. Comm., 647 (1974).
D. D. Chapman,J. K. Elwood,D. W. Heseltine,H. M. Hess, andD. W. Kurts, J. Org. Chem., 42, 2474 (1977).
Z. Lin,Z. Nan,Z. Zhang, andY. Huang, Youji Huaxue, 369 (1984); Chem. Abs.,102, 78699 (1985).
A. A. Shachkus andYu. A. Degutis, Khim. Geterotsikl. Soedin., 481 (1987).
A. A. Shachkus andYu. A. Degutis, Khim. Geterotsikl. Soedin., 1055 (1990).
R. Robinson andJ. E. Saxton, J. Chem. Soc., 3136 (1950).
R. Robinson andJ. E. Saxton, J. Chem. Soc., 976 (1952).
I. Jirkovsky,G. Santroch,R. Baudy, andG. Oshiro, J. Med. Chem., 30, 388 (1987).
R. A. Bit,P. D. Davis,C. H. Hill,E. Keech, andD. R. Vesey, Tetrahedron, 47, 4645 (1991).
G. W. Gribble,M. G. Saulnier, Obaza-Nutaitie, and D. M. Kecha, J. Org. Chem., 57, 5891 (1992).
C.-P. Chuang andS.-F. Wang, Tetrahedron Lett., 35, 1283 (1994).
S.-F. Wang andC.-P. Chuang, Heterocycles, 45, 347 (1997).
J.-Y. Merour,S. Piroelle, andF. Cossais, Heterocycles, 36, 1287 (1993).
W. Flitsch andK. Pandl, Lieb. Ann. Chem., 649 (1987).
F. Z. Galin,S. N. Lakeev, andG. A. Tolstikov, Khim. Geterotsikl. Soedin., 1693 (1989).
F. Z. Galin,S. N. Lakeev, andG. A. Tolstikov, Izv. Akad. Nauk. Ser. Khim., 165 (1996).
F. Z. Galin,S. N. Lakeev, andG. A. Tolstikov, Izv. Akad. Nauk. Ser. Khim., 2008 (1997).
F. Santavy, The Alkaloids (Ed. R. H. F. Manske), Academic Press, New York (1977), Vol. 17, p. 385.
A. R. Katritzky,C. N. Fali, andJ. Li, J. Org. Chem., 62, 4148 (1997).
R. Katritzky,X. Wang,L. Xie, andD. Toader, J. Org. Chem., 63, 3445 (1998).
J. Heer andK. Hoffmann, Helv. Chim. Acta, 39, 1820 (1956).
H. H. Wasserman andW. R. Waterfield, Chem. Ind., 1220 (1961).
H. A. Smith andC. W. Halley, J. Am. Chem. Soc., 80, 3714 (1958).
A. Kh. A. Rodriges,A. T. Soldatenkov,S. A. Soldatova,A. Yu. Samal'oa,Kh. Obando, andN. S. Prostakov, Khim. Geterotsikl. Soedin., 1233 (1993).
L. I. Krivenko,A. T. Soldatenkov,O. V. Zvolinskii,J. N. Kuleshova,V. N. Khrustalev,V. N. Guryshev, andS. A. Soldatova, Khim. Geterotsikl. Soedin., 793 (1997).
L. I. Krivenko, Thesis for Candidate of Chemical Sciences [in Russian], Moscow (1998).
A. T. Soldatenkov,M. M. Kolyadina,L. N. Kuleshova, andV. N. Khrustalev, Khim. Geterotsikl. Soedin., 955 (1996).
R. Hurt andN. Filipescu, J. Am. Chem. Soc., 94, 3649 (1972).
Y. T. Park,K. S. Kirn,I. H. Lee,Ch. H. Goo, andY. Ch. Park, Bull. Korean Chem. Soc., 14, 152 (1993); Chem. Abs.,119, 72476 (1993).
R. Robinson andS. Sugasawa, J. Chem. Soc., 789 (1932).
C. Schopf andK. Thierfelder, Lieb. Ann. Chem., 497, 22 (1932).
F. Santavy, The Alkaloids (Ed. R. H. F. Manske), Academic Press, New York (1970), Vol. 12, p. 333.
A. Deegan andF. Rose, J. Chem. Soc., 2756 (1971).
A. Ohsawa,T. Kawaguchi, andH. Igeta, J. Org. Chem., 47, 3497 (1982).
A. Ohsawa,T. Kawaguchi, andH. Igeta, Synthesis, 1037 (1983).
T. Kametani,K. Fukumoto, andT. Nakano, J. Heterocycl. Chem., 9, 1363 (1972).
T. Kametani andK. Ogasawara, Chem. Pharm. Bull., 16, 1498 (1968).
T. Kametani andK. Ogasawara, J. Chem. Soc., 2208 (1967).
F. Benington andR. D. Morin, J. Org. Chem., 32, 1050 (1967).
L. Beckwith andS. W. Westwood, Tetrahedron, 45, 5269 (1989).
R. Artis,I.-S. Cho,S. Jaime-Figueroa,J. M. Muchowski, J. Org. Chem., 59, 2456 (1994).
A. P. Dobbs,K. Jones, andT. Veal, Tetrahedron Lett., 36, 4857 (1995).
T. Okano,T. Sakaida, andS. Eguchi, J. Org. Chem., 61, 8826 (1996).
S. Caddick,K. Aboutayab,K. Jenkins, andR. I. West, J. Chem. Soc. Perkin Trans. I, 70, 675 (1996).
A. P. Dobbs,K. Jones, andT. Veal, Tetrahedron Lett., 38, 5383 (1997).
J. Braun andJ. Nelles, Berichte, 70, 1767 (1937).
A. T. Soldatenkov,M. V. Bagdali,A. A. Fomichev, andN. S. Prostakov, Zh. Org. Khim., 18, 902 (1982).
A. T. Soldatenkov,M. V. Bagdali,A. A. Fomichev, andN. S. Prostakov, Zh. Org. Khim., 19, 1326 (1983).
S. A. Soldatova,A. Kh. A. Rodriges, andA. T. Soldatenkov, Khim. Geterotsikl. Soedin., 79 (1994).
T. Borrows,D. O. Holland, andJ. Kenyon, J. Chem. Soc., 1077 (1946).
Y. Arota,T. Ohashi, andK. Uwai, J. Pharm. Soc. (Japan), 75, 265 (1955).
I. Anitha andP. K. Rajan, J. Indian Chem. Soc., 66, 460 (1989).
W. Kiel andF. Krohnke, Chem. Ber., 105, 3709 (1972).
K. Matsumoto,T. Uchida,K. Aoyama,M. Nishikawa,T. Kuroda, andT. Okamoto, J. Heterocycl. Chem., 25, 1793 (1988).
F. Krohnke andH. Schmei, Berichte, 70, 1728 (1937).
W. Augustein andF. Krohnke, Lieb. Ann. Chem., 697, 158 (1966).
D. B. Reuschling andF. Krohnke, Chem. Ber., 104, 2103 (1971).
D. B. Reuschling andF. Krohnke, Chem. Ber., 104, 2110 (1971).
F. Sartori, Chem. Rev., 63, 279 (1963).
B. Suryanarayana andB. D. Tilak, Current Sci. (India), 22, 171 (1953).
B. Suryanarayana andB. D. Tilak, Proc. Indian Acad. Sci., 39, 185 (1954).
F. Pratt,R. W. Luckenbaugh, andR. L. Erickson, J. Org. Chem., 19, 176 (1954).
F. Pratt,R. G. Rice, andR. W. Luckenbaugh, J. Am. Chem. Soc., 79, 1212 (1957).
F. Pratt andJ. C. Keresztesy, J. Org Chem., 32, 49 (1967).
R. Ayyangar,A. G. Lugade, andM. N. Rajadhyksha, Indian J. Chem., 25, 1126 (1986).
J. A. van Allan,G. A. Reynolds, andR. E. Adel, J. Org. Chem., 28, 3502 (1963).
P. A. Barret andK. A. Chambers, J. Chem. Soc., 338 (1958).
D. Saeva andH. R. Luss, J. Org. Chem., 53, 1804 (1988).
I. Dainis, Austr. J. Chem., 25, 1549 (1972).
K. Dalton andT. Teitei, Austr. J. Chem., 22, 1525 (1969).
V. I. Terenin,E. V. Kabanova,N. A. Baranova, andYu. G. Bundel', Khim. Geterotsikl. Soedin., 331 (1995).
A. T. Soldatenkov,Zh. Ntaganda,S. A. Soldatova,Kh. A. R. Alarkon,B. N. Anisimov, andN. I. Golovtsov, Khim. Geterotsikl. Soedin., 786 (1999).
Zh. Ntaganda, Thesis for Candidate of Chemical Sciences [in Russian], Moscow (1996).
Zh. Ntaganda,S. A. Soldatova,A. Kh. A. Rodriges,B. N. Anisimov, andA. T. Soldatenkov, Khim. Geterotsikl. Soedin., 83 (1994).
N. S. Prostakov,A. T. Soldatenkov,M. V. Bagdali,O. S. Brindkha,V. I. Kuznetsov,V. A. Rezakov, andA. A. Fomichev, Khim. Geterotsikl. Soedin., 1371 (1984).
Zh. Ntaganda,S. A. Soldatova,B. N. Anisimov,A. Kh. A. Rodriges, andA. T. Soldatenkov, Khim. Geterotsikl. Soedin., 217 (1994).
S. A. Soldatova,A. Kh. A. Rodriges,Z. A. Mamyrbekova,L. I. Krivenko,Z. H. Ntaganda,M. A. Ryashentseva, andA. T. Soldatenkov, Khim. Geterotsikl. Soedin., 377 (1994).
Kh. A. R. Alarkon,S. A. Soldatova,A. T. Soldatenkov,M. A. Ryashentseva, andN. S. Prostakov, Izv. Akad. Nauk. Ser. Khim., 1433 (1991).
D. Lednicer,A. L. Mitscher, andG. I. Georg, The Organic Chemistry of Drug Synthesis, Vol. 4, Wiley, New York (1990), p 211.
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Soldatenkov, A.T., Kolyadina, N.M. Chemistry of Indolopyridines with a Bridgehead Heteroatom. (Review). Chemistry of Heterocyclic Compounds 37, 1059–1091 (2001). https://doi.org/10.1023/A:1013249730703
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DOI: https://doi.org/10.1023/A:1013249730703