Diene-transmissive hetero-Diels-Alder reaction of cross-conjugated azatrienes: A novel and efficient method for the synthesis of ring-fused nitrogen heterocycles

Chemical Communications

Volumn , Issue 11, 1997, Pages 1013-1014

  Saito, Takao ^a   Kimura, Hiroaki ^a   Chonan, Tomomichi ^a   Soda, Takayuki ^a   Karakasa, Takayuki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002310308     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701575e     Document Type: Article

References (30)

1. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
2. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
3. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
4. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
5. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
6. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
7. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
8. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
9. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
10. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
11. For excellent reviews and monographs on such sequential, multistep processes (the so-called domino, tandem or cascade strategy) involving a Diels-Alder reaction, see F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley, New York, 1990; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; L. F. Tietze, Chem. Rev., 1996, 96, 115; S. E. Denmark and A. Thorarensen, Chem. Rev., 1996, 96, 137; J. D. Winkler, Chem. Rev., 1996, 96, 167. For recent publications, see 'Cascade Reactions', Tetrahedron Symposia-in-Print, 1996, 52, 11 385; K. H. Ang, S. Brase, A. G. Steinig, F. E. Meyer, A. Llebaria, K. Voigt and A. de Meijere, Tetrahedron, 1996, 52, 11 503; S. E. Denmark and C. B. W. Senanayake, Tetrahedron, 1996, 52, 11 579; A. Franz, P.-Y. Eschler, M. Thrin and R. Neier, Tetrahedron, 1996, 52, 11 643; A. Hosomi, T. Masunari, Y. Tominaga, T. Yanagi and M. Hojo, Tetrahedron Lett., 1990, 31, 6201.
12. O. Tsuge, S. Kanemasa, E. Wada and H. Sakoh, Yuki Gosei Kagaku Kyokaishi, 1986, 44, 756; O. Tsuge, E. Wada and S. Kanemasa, Chem. Lett., 1983, 239; O. Tsuge, E. Wada, S. Kanemasa and H. Sakoh, Bull. Chem. Soc. Jpn., 1984, 57, 3221; O. Tsuge, S. Kanemasa, H. Sakoh and E. Wada, Bull. Chem. Soc. Jpn., 1984, 57, 3234; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1985, 58, 3312; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1986, 59, 1869.
13. O. Tsuge, S. Kanemasa, E. Wada and H. Sakoh, Yuki Gosei Kagaku Kyokaishi, 1986, 44, 756; O. Tsuge, E. Wada and S. Kanemasa, Chem. Lett., 1983, 239; O. Tsuge, E. Wada, S. Kanemasa and H. Sakoh, Bull. Chem. Soc. Jpn., 1984, 57, 3221; O. Tsuge, S. Kanemasa, H. Sakoh and E. Wada, Bull. Chem. Soc. Jpn., 1984, 57, 3234; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1985, 58, 3312; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1986, 59, 1869.
14. O. Tsuge, S. Kanemasa, E. Wada and H. Sakoh, Yuki Gosei Kagaku Kyokaishi, 1986, 44, 756; O. Tsuge, E. Wada and S. Kanemasa, Chem. Lett., 1983, 239; O. Tsuge, E. Wada, S. Kanemasa and H. Sakoh, Bull. Chem. Soc. Jpn., 1984, 57, 3221; O. Tsuge, S. Kanemasa, H. Sakoh and E. Wada, Bull. Chem. Soc. Jpn., 1984, 57, 3234; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1985, 58, 3312; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1986, 59, 1869.
15. O. Tsuge, S. Kanemasa, E. Wada and H. Sakoh, Yuki Gosei Kagaku Kyokaishi, 1986, 44, 756; O. Tsuge, E. Wada and S. Kanemasa, Chem. Lett., 1983, 239; O. Tsuge, E. Wada, S. Kanemasa and H. Sakoh, Bull. Chem. Soc. Jpn., 1984, 57, 3221; O. Tsuge, S. Kanemasa, H. Sakoh and E. Wada, Bull. Chem. Soc. Jpn., 1984, 57, 3234; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1985, 58, 3312; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1986, 59, 1869.
16. O. Tsuge, S. Kanemasa, E. Wada and H. Sakoh, Yuki Gosei Kagaku Kyokaishi, 1986, 44, 756; O. Tsuge, E. Wada and S. Kanemasa, Chem. Lett., 1983, 239; O. Tsuge, E. Wada, S. Kanemasa and H. Sakoh, Bull. Chem. Soc. Jpn., 1984, 57, 3221; O. Tsuge, S. Kanemasa, H. Sakoh and E. Wada, Bull. Chem. Soc. Jpn., 1984, 57, 3234; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1985, 58, 3312; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1986, 59, 1869.
17. O. Tsuge, S. Kanemasa, E. Wada and H. Sakoh, Yuki Gosei Kagaku Kyokaishi, 1986, 44, 756; O. Tsuge, E. Wada and S. Kanemasa, Chem. Lett., 1983, 239; O. Tsuge, E. Wada, S. Kanemasa and H. Sakoh, Bull. Chem. Soc. Jpn., 1984, 57, 3221; O. Tsuge, S. Kanemasa, H. Sakoh and E. Wada, Bull. Chem. Soc. Jpn., 1984, 57, 3234; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1985, 58, 3312; S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1986, 59, 1869.
18. S. Motoki, Y. Matsuo and Y. Terauchi, Bull. Chem Soc. Jpn., 1990, 63, 284.
19. T. Saito, U. Kimura, K. Sakamaki, T. Karakasa and S. Moriyama, Chem. Commun., 1996, 811.
20. O. Tsuge, T. Hatta, K. Yakata and H. Maeda, Chem. Lett., 1994, 1833; O. Tsuge, T. Hatta, H. Yoshitomi, K. Kurosaka, T. Fujiwara, H. Maeda and A. Kakehi, Heterocycles, 1995, 41, 225.
21. O. Tsuge, T. Hatta, K. Yakata and H. Maeda, Chem. Lett., 1994, 1833; O. Tsuge, T. Hatta, H. Yoshitomi, K. Kurosaka, T. Fujiwara, H. Maeda and A. Kakehi, Heterocycles, 1995, 41, 225.
22. G. Spino and G. Liu, J. Org. Chem., 1993, 58, 817.
23. D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic. New York, 1987; D. E. Boger, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and L. A. Paquett, Pergamon, Oxford, 1991, vol. 5, p. 451; J. Barluenga, Adv. Heterocycl. Chem., 1993, 57, 1.
24. D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic. New York, 1987; D. E. Boger, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and L. A. Paquett, Pergamon, Oxford, 1991, vol. 5, p. 451; J. Barluenga, Adv. Heterocycl. Chem., 1993, 57, 1.
25. D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic. New York, 1987; D. E. Boger, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and L. A. Paquett, Pergamon, Oxford, 1991, vol. 5, p. 451; J. Barluenga, Adv. Heterocycl. Chem., 1993, 57, 1.
26. J. Barluenga, I. Merino and F. Palacios, J. Chem. Soc., Perkin Trans. 1, 1991, 341; K. Eiter and H. Oediger, Justus Liebigs Ann. Chem., 1965, 682, 62.
27. J. Barluenga, I. Merino and F. Palacios, J. Chem. Soc., Perkin Trans. 1, 1991, 341; K. Eiter and H. Oediger, Justus Liebigs Ann. Chem., 1965, 682, 62.
28. D. L. Boger, W. E. Cobett, T. T. Curran and A. M. Kasper, J. Am. Chem. Soc., 1991, 113, 1713.
29. S. Moriyama, T. Karakasa, T. Inoue, K. Kurashima, S. Satsumabayashi and T. Saito, Synlett, 1996, 72.
30. LAOCOON III, D. F. Detar, Computer Programs for Chemistry, W. A. Benjamin, Inc., New York 1968, vol. 1, p 10; Chemistry and Software No. 8007 program was used. The following JCPE (Japan Chemistry Program Exchange) programs were used: CONFLEX (program No. P040), MOPAC 93 (program No. P081), and 3JHH2 (program No. P012).