Abstract
Published data on the synthesis and chemical transformations of 3,4-2H-dihydropyrroles (Δ1-pyrrolines) are analyzed and reviewed for the first time.
Similar content being viewed by others
REFERENCES
K. Hasse and H. Maisack, Biochem. Z., 327, 296 (1955).
K. Hasse and H. Maisack, Naturwissenschaft, 42, 627 (1955).
P. J. Mann and W. R. Smithies, Biochem. J., 61, 89 (1955); Chem. Abstr., 49, 15992 (1955).
A. J. Clarke and P. J. Mann, Biochem. J., 71, 596 (1959).
P. S. Callery, M. S. B. Nayar, L. A. Geelhaar, M. Stogniew, and E. M. Jakubowski, Biomed. Mass Spectrom., 7, 525 (1980); Chem. Abstr., 95, 4071 (1981).
A. Ch. Andersson, S. Henningsson, L. Persson, and E. Rosengren, Agents Actions, 8, 380 (1978); Chem. Abstr., 89, 160750 (1978).
A. Ch. Andersson, S. Henningsson, L. Persson, and E. Rosengren, Acta Physiol. Scand., 102, 159 (1978); Chem. Abstr., 88, 84973 (1978).
A. Ch. Andersson and S. Henningsson, Agents Actions, 10, 104 (1980); Chem. Abstr., 92, 212962 (1980).
P. S Callery, M. S. B. Nayar, and L. A. Geelhaar, Biomed. Mass Spectrom., 11, 118 (1984); Chem. Abstr., 101, 19675 (1984).
A. Lüttringhaus, J. Jander, and R. Schneider, Chem. Ber., 92, 1756 (1959).
Ya. F. Oshis, A. A. Anderson, and M. V. Shimanskaya, USSR Inventor's Certificate 891658; Ref. Zh. Khim., 17 N203P (1982).
Ya. F. Oshis, A. A. Anderson, and M. V. Shimanskaya, Izv. Akad. Nauk LatvSSR, Ser. Khim., 67 (1987).
U. Bachrach, Nature, 194, 377 (1962).
U. Bachrach, J. Biol. Chem., 237, 3443 (1962)
E. C. Woff, M. H. Park, and J. E. Folk, J. Biol. Chem., 265, 4793 (1990).
H. Bock and R. Dammel, Chem. Ber., 120, 1971 (1987).
J.-C. Guillemin and J.-M. Denis, Tetrahedron, 44, 4431 (1988).
S. Sugasawa and S. Ushioda, Tetrahedron, 5, 48 (1959).
T. Kercher and T. Livinghouse, J. Org. Chem., 62, 805 (1997).
A. A. Anderson, T. G. Andronikashvili, L. Ya. Laperashvili, Ya. F. Oshis, G. V. Tsitsishvili, M. V. Shimanskaya, and S. P. Yurel', Application of Zeolites in Catalysis. Abstracts of All-Union Conference [in Russian], Moscow (1981), p. 234.
Ya. F. Oshis, A. A. Anderson, and M. V. Shjimanskaya, Izv. Akad. Nauk. LatvSSR, Ser. Khim., 408 (1981).
J. Kijenski, P. J. Niedzielski, and A. Baiker, Appl. Catal., 53, 107 (1989).
K. Yoshikawa, L. M. Libbey, W. Y. Cobb, and E. A. Day, J. Food Sci., 30, 991 (1965); Chem. Abstr., 64, 6933 (1966).
G. Baxter, J. C. Melville, and D. J. Robins, Synlett, 359 (1991).
K. Hasse and G. Schmid, Biochem. Z., 337, 480 (1963).
H. J. Vogel and B. D. Davis, J. Am. Chem. Soc., 14, 109 (1952).
G. G. Evans, J. Am. Chem. Soc., 73, 5230 (1951).
H. Gershon and A. Scala, J. Org. Chem., 26, 2347 (1961).
E. Kato, K. Yamamoto, Yo. Kawashima, T. Watanabe, M. Oya, T. Iso, and J. Iwao, Chem. Pharm. Bull., 33, 4836 (1985).
J. Ackermann, M. Matthes, and Ch. Tamm, Helv. Chim. Acta, 73, 122 (1990).
A. Giovannini, D. Savoia, and A. Umani-Ronchi, J. Org. Chem., 54, 228 (1989).
E. Beausoleil, B. L'Archeveque, L. Belec, M. Atfani, and W. D. Lubell, J. Org. Chem., 61, 9447 (1996).
A. Mkairi and J. Hamelin, Tetrahedron Lett., 28, 1397 (1987).
A. Van der Werf and R. M. Kellogg, Tetrahedron Lett., 32, 3727 (1991).
W. B. Jakoby and J. Fredericks, J. Biol. Chem., 234, 2145 (1959).
J. E. Cragg, R. B. Herbert, F. B. Jackson, Ch. J. Moody, and I. T. Nicolson, J. Chem. Soc., Perkin Trans. I, 2477 (1982).
D. W. Lundgren, H. A. Lloyd, and J. Hankins, Biochem. Biophys. Res. Commun., 97, 667 (1980).
J. C. Richards and I. D. Spenser, Tetrahedron, 39, 3549 (1983).
K. T. Okamoto and J. Clardy, Tetrahedron Lett., 25, 2937 (1984).
R. B. Herbert, F. B. Jackson, and I. T. Nicolson, J. Chem. Soc., Perkin Trans. I, 825 (1984).
G. B. Itoua and J.-Y. Laronze, Synthesis, 353 (1987).
Y. Watanabe, J. Yamamoto, M. Akazome, T. Kondo, and T. Mitsudo, J. Org. Chem., 60, 8328 (1995).
J. H. Burckhalter and J. H. Short, J. Org. Chem., 23, 1281 (1958).
E. Leete, M. R. Chedekel, and G. B. Bodem, J. Org. Chem., 37, 4465 (1972).
M. Vaultie, P. H. Lambert, and R. Carrie', Bull. Soc. Chim. Fr., 83 (1986).
N. De Kimpe, K. A. Tehrami, Ch. Stevens, and P. De Cooman, Tetrahedron, 53, 3693 (1997).
K. R. Prabhu, P. S. Sivanand, and S. Chandrsekaran, Synlett, 47 (1998).
P. M. Maginnity and J. B. Cloke, J. Am. Chem. Soc., 73, 49 (1951).
P. J. A. Demoen and A. J. Janssen, J. Am. Chem. Soc., 81, 6281 (1959).
S. Wagaw, R. A. Rennels, and S. L. Burchwald, J. Am. Chem. Soc., 119, 8451 (1997).
M. Murakami, N. Hasegawa, T. Nagatomi, and Yo. Ito, Heterocycles, 47, 85 (1998).
J. P. Dinnocenzo, H. Zuilhof, D. R. Lieberman, T. R. Simpson, and M. W. Me Kechney, J. Am. Chem. Soc., 119, 994 (1997).
K. Osowska-Pacewicka and A. Zwierzak, Synth. Commun., 28, 1127 (1998); Chem. Abstr., 128, 294654 (1998).
J. Ahman, T. Jarevang, and P. Somfai, J. Org. Chem., 61, 8148 (1996).
Yu. Nomura, K. Ogawa, Yo. Takeuchi, and Sh. Tomoda, Chem. Lett., 693 (1997).
K. Ogawa, Yu. Nomura, Yo. Takeuchi, and Sh. Tomoda, J. Chem. Soc., Perkin Trans. I, 3031 (1982).
M. Ochiai, M. Inenaga, Yo. Nagao, R. M. Moriarty, R. K. Vaid, and M. P. Duncan, Tetrahedron Lett., 29, 6917 (1988).
H. Rapoport and N. Castagnoli, Jr., J. Am. Chem. Soc., 84, 2178 (1962).
E. Rosenberg, Sh. E. Kabir, K. I. Hardcastle, M. Day, and E. Wolf, Organometallics, 9, 2214 (1990); Ref. Zh. Khim., 146226 (1991).
J.-C. Guillemin, J.-M. Denis, M. C. Lasne, and J.-L. Ripoll, Tetrahedron, 44, 4447 (1988).
C. Schopf, Germ. Patent 1054088; Chem. Abstr., 55, 8439 (1961).
H. Poisel, Monatsh. Chem., 109, 925 (1978).
G. Piancatelli and A. Scettri, Tetrahedron, 32, 1745 (1976).
U. Leutenegger, G. Umbricht, Ch. Fahrni, P. Matt, and A. Pfaltz, Tetrahedron, 48, 2143 (1992).
D. StC. Black, M. C. Bowyer, and N. Kumar, Tetrahedron, 53, 8573 (1997).
D. Spitzner, Synthesis, 242 (1977).
J. I. Seemzn, Synthesis, 498 (1977).
J. Bielawski, S. Brandange, and L. Lindblom, J. Heteterocycl. Chem., 15, 97 (1978).
B. L. Feringa and J. F. G. A. Jansen, Tetrahedron Lett., 27, 507 (1986).
B. P. Mundy and B. R. Larsen, Synth. Commun., 2, 197 (1972).
B. P. Mundy, B. R. Larsen, L. F. Me Kenzie, and G. Braden, J. Org. Chem., 37, 1635 (1972).
B. P. Mundy, K. B. Lipkowitz, M. Lee, and B. R. Larsen, J. Org. Chem., 39, 1963 (1974).
P. D. Bragg and L. Y. Hough, J. Chem. Soc., 4050 (1958).
G. Grue-Sorensen and I. D. Spenser, Can. J. Chem., 60, 643 (1982).
K. Hasse, J. Hess, and H. W. Hornig, Chem. Ber., 104, 2420 (1971).
K. Endo, K. Hirayama, Yu. Aota, K. Seya, H. Asakura, and K. Hisamichi, Heterocycles, 47, 865 (1998).
Yu. A. Zolotarev, E. V. Laskatelev, V. S. Kozik, E. M. Dorokhova, S. T. Rozenberg, Yu. A. Borisov, and N. F. Myasoedov, Izv. Akad. Nauk. Ser. Khim., 1820 (1997).
K. Shiosaki and H. Rapoport, J. Org. Chem., 50, 1229 (1985).
J. S. Petersen, G. Pels, and H. Rapoport, J. Am. Chem. Soc., 106, 4539 (1984).
M. H. Howard, F. J. Sardina, and H. Rapoport, J. Org. Chem., 55, 2829 (1990).
K. Warning and M. Mitzlaff, German Patent 2636098; Ref. Zh. Khim., 1 N235 P (1979).
T. Abe and H. Fukaya, Jpn. Patent 08165275; Chem. Abstr., 125, 221580 (1996).
J. Ezquerra, A. Escribano, and A. Rubio, Tetrahedron Asymmetry, 7, 2613 (1996).
P. Rademacher, P. Heymanns, R. Münzenberg, H. Wöll, K. Kowski, and R. Poppek, Chem. Ber., 127, 2073 (1994).
L. Knorr and P. Rabe, Berichte, 34, 3491 (1901).
L. H. Andrews and M. McElvain, J. Am. Chem. Soc., 51, 887 (1928).
P. de March, M. Figueredo, J. Font, T. Gallagher, and S. Milan, J. Chem. Soc. Chem. Commun., 2097 (1995).
A. Eschenmoser and C. E. Wintner, Science, 196, 1410 (1977).
H. Quasi, A. Fuss, and W. Nüdling, Eur. J. Org. Chem., 317 (1998).
H. Kayakiri, Sh. Takase, H. Setoi, I. Uchida, H. Terano, and M. Hashimoto, Tetrahedron Lett., 29, 1725 (1988).
N. Bojkova and H. Heimgartner, Heterocycles, 47, 781 (1998).
F. Clerici, M. L. Gelmi, D. Pocar, and R. Rondena, Tetrahedron, 51, 9985 (1995).
D. W. Fuhlhage and C. A. Van der Werf, J. Am. Chem. Soc., 80, 6249 (1958).
H. Mohrle, G. Troster, M. Linden, D. Mootz, and H. Wunderlich, Tetrahedron, 37, 2881 (1981).
G. Maio, P. A. Tardella, Proc. Chem. Soc., 224 (1963).
H. Kayakiri, K. Nakamura, Sh. Takase, H. Setoi, I. Uchida, H. Terano, M. Hashimoto, T. Tada, and S. Koda, Chem. Pharm. Bull., 39, 2807 (1991).
Yo. J. Kirn and T. Kitahara, Tetrahedron Lett., 38, 3423 (1997).
Sh. Takayama, R. Martin, W. Jiangyue, K. Laslo, G. Siuzdak, and Ch.-H. Wong, J. Am. Chem. Soc., 119, 8146 (1997).
Z.-M. Qiu and D. J. Burton, Tetrahedron Lett., 35, 4319 (1994).
Z.-M. Qiu and D. J. Burton, Tetrahedron Lett., 36, 5119 (1995).
O. Tsuge, Sh. Kanemasa, and K. Matsuda, J. Org. Chem., 51, 1997 (1986).
O. Tsuge, T. Hatta, Yo. Kakura, H. Tashiro, H. Maeda, and A. Kakehi, Chem. Lett., 945 (1997).
C. Alvarez-Ibarra, A. G. Csaky, I. L. de Silanes, and M. L. Quiroga, J. Org. Chem., 62, 479 (1997).
Sk. R. Amin and W. E. Crowe, Tetrahedron Lett., 38, 7487 (1997).
B. Rugewitz-Blackholm and M. Wiessler, Liebigs Ann. Chem., 583 (1987).
E. W. Petrillo, Jr., and E. P. Spitzmiller, Tetrahedron Lett., 4929 (1979).
S. Barbati, J.-L. Clement, C. Frejaville, J.-C. Bouteiller, P. Tordo, J.-C. Michel, and J.-C. Yadan, Synthesis, 2036 (1999).
X.-Yu. Jiao, M. Borloo, Ch. Verbruggen, and A. Haemers, Tetrahedron Lett., 35, 1103 (1994).
F. E. Scully, Jr., J. Org. Chem., 45, 1515 (1980).
M. Nakamura, A. Hirai, and E. Nakamura, J. Am. Chem. Soc., 118, 8489 (1996).
J. M. Grisar and G. P. Claxton, German Patent 2417782; Chem. Abstr., 82, 72580 (1975).
J. M. Grisar and G. P. Claxton, German Patent 2418480; Chem. Abstr., 82, 72794 (1975).
J. M. Grisar, G. P. Claxton, and K. T. Stewart, Synthesis, 284 (1974).
J. M. Grisar, G. P. Claxton, K. T. Stewart, R. D. MacKenzie, and T. Kariya, J. Med. Chem., 19, 1195 (1976).
R. B. Herbert, F. B. Jackson, and I. T. Nicolson, J. Chem. Soc. Chem. Commun., 450 (1976).
V. K. Mangla and D. S. Bhakuni, Indian J. Chem., 19B, 931 (1980).
V. K. Mangala and D. S. Bhakuni, Indian J. Chem., 19B, 748 (1980).
K. Iwasa, M. Kamigauchi, N. Takao, and W. Wiegrebe, J. Nat. Prod., 51, 172 (1988); Ref. Zh. Khim., 15E122 (1988).
S. J. Danishefsky and C. Vogel, J. Org. Chem., 51, 3915 (1986).
L. S. Hegedus and D. B. Miller, Jr., J. Org. Chem., 54, 1241 (1989).
L. S. Hegedus, R. Imwinkelried, M. Alarid-Sargent, D. Dvorak, and Y. Satoh, J. Am. Chem. Soc., 112, 1109 (1990).
Z. Szakonyi, F. Fulop, G. Bernath, and P. Sohar, Magy. Kern. Foly, 104, 17 (1998); Chem. Abstr., 128, 192622 (1998).
F. T. Smith, J. De Ruiter, and D. A. Carter, J. Heterocycl. Chem., 26, 1815 (1989).
F. T. Smith and R. V. Atigadda, J. Heterocycl. Chem., 28, 1813 (1991).
B. M. Goldschmidt, J. Org. Chem., 27, 4057 (1962).
K. G. Nazarenko, V. A. Kovtunenko, A. M. Demchenko, and M. V. Kornilov, Ukr. Khim. Zh., 62, 42 (1996).
J. J. Tufariello, 1,3-Dipolar Cycloaddition Chemistry, (Ed. A. Padwa), Wiley, New York, (1984), Vol. 2, Ch. 9.
G. A. Kraus and K. Neuenschwander, J. Org. Chem., 46, 4791 (1981).
J. Barluenga, M. Tomas, V. Kouznetsov, A. Suarez-Sobrino, and E. Rubio, J. Org. Chem., 61, 2185 (1996).
R. F. Nutt and M. M. Joullie, J. Am. Chem. Soc., 104, 5852 (1982).
P. S. Callery, L. A. Geelhaar, M. S. B. Nayar, M. Stogniew, and K. G. Rao, J. Neurochem., 38, 1063 (1982); Chem. Abstr., 97, 85941 (1982).
M. Anbazhagan, A. N. Dixit, and S. Rajappa, J. Chem. Soc., Perkin Trans. I, 2421 (1997).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Shvekhgeimer, MG.A. Methods for the Synthesis of 3,4-2H-Dihydropyrroles (Δ1-Pyrrolines) and Their Chemical Transformations. (Review). Chemistry of Heterocyclic Compounds 39, 405–448 (2003). https://doi.org/10.1023/A:1024753027533
Issue Date:
DOI: https://doi.org/10.1023/A:1024753027533