Microwave assisted domino Knoevenagel condensation/6π-electron electrocyclization reactions for the rapid and efficient synthesis of substituted 2H,5H-pyrano[4,3-b]pyran-5-ones and related heterocycles

QSAR and Combinatorial Science

Volumn 23, Issue 10, 2004, Pages 895-898

  Leutbecher, Heiko ^a   Conrad, Jürgen ^a   Klaiber, Iris ^a   Beifuss, Uwe ^a  

^a UNIVERSITY OF HOHENHEIM   (Germany)

Author keywords

Domino reaction; Electrocyclic reaction; Heterocycles; Microwaves

Indexed keywords

CONDENSATION REACTIONS; ORGANIC COMPOUNDS; REACTION KINETICS;

DOMINO REACTIONS; EFFICIENT SYNTHESIS; ELECTROCYCLIC REACTIONS; ELECTROCYCLIZATION REACTIONS; HETEROCYCLES; HETEROCYCLIC RINGS; KNOEVENAGEL CONDENSATION; MEDICINAL CHEMISTRY; MICROWAVE-ASSISTED; RAPID SYNTHESIS;

CONDENSATION;

PYRAN DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COMBUSTION; ELECTRON TRANSPORT; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MICROWAVE IRRADIATION; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 12344268799     PISSN: 1611020X     EISSN: None     Source Type: Journal    
DOI: 10.1002/qsar.200420048     Document Type: Article

References (44)

1. For monographs, see: a) K. C. Nicolaou, R. Hanko, W. Hartwig (Eds.), Handbook of Combinatorial Chemistry: Drugs, Catalysts, Materials, Wiley-VCH, Weinheim, 2002; b) W. Bannwarth, E. Felder (Eds.), Combinatorial Chemistry, Wiley-VCH, Weinheim, 2000; c) G. Jung (Ed.), Combinatorial Chemistry: Synthesis, Analysis, Screening, Wiley-VCH, Weinheim, 1999; d) S. R. Wilson, A. W. Czarnik (Eds.), Combinatorial Chemistry: Synthesis and Application, Wiley, New York, 1997.
2. For monographs, see: a) K. C. Nicolaou, R. Hanko, W. Hartwig (Eds.), Handbook of Combinatorial Chemistry: Drugs, Catalysts, Materials, Wiley-VCH, Weinheim, 2002; b) W. Bannwarth, E. Felder (Eds.), Combinatorial Chemistry, Wiley-VCH, Weinheim, 2000; c) G. Jung (Ed.), Combinatorial Chemistry: Synthesis, Analysis, Screening, Wiley-VCH, Weinheim, 1999; d) S. R. Wilson, A. W. Czarnik (Eds.), Combinatorial Chemistry: Synthesis and Application, Wiley, New York, 1997.
3. For monographs, see: a) K. C. Nicolaou, R. Hanko, W. Hartwig (Eds.), Handbook of Combinatorial Chemistry: Drugs, Catalysts, Materials, Wiley-VCH, Weinheim, 2002; b) W. Bannwarth, E. Felder (Eds.), Combinatorial Chemistry, Wiley-VCH, Weinheim, 2000; c) G. Jung (Ed.), Combinatorial Chemistry: Synthesis, Analysis, Screening, Wiley-VCH, Weinheim, 1999; d) S. R. Wilson, A. W. Czarnik (Eds.), Combinatorial Chemistry: Synthesis and Application, Wiley, New York, 1997.
4. For monographs, see: a) K. C. Nicolaou, R. Hanko, W. Hartwig (Eds.), Handbook of Combinatorial Chemistry: Drugs, Catalysts, Materials, Wiley-VCH, Weinheim, 2002; b) W. Bannwarth, E. Felder (Eds.), Combinatorial Chemistry, Wiley-VCH, Weinheim, 2000; c) G. Jung (Ed.), Combinatorial Chemistry: Synthesis, Analysis, Screening, Wiley-VCH, Weinheim, 1999; d) S. R. Wilson, A. W. Czarnik (Eds.), Combinatorial Chemistry: Synthesis and Application, Wiley, New York, 1997.
5. For monographs, see: a) B. L. Hayes, Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, NC, 2002; b) A. Loupy (Ed.), Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, 2002; for recent reviews, see: c) Y. Xu, Q.-X. Guo, Heterocycles 2004, 63, 903-974; d) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199-9223; e) P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225-9283; for information from the internet, see: f) http://www.maos.net.
6. For monographs, see: a) B. L. Hayes, Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, NC, 2002; b) A. Loupy (Ed.), Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, 2002; for recent reviews, see: c) Y. Xu, Q.-X. Guo, Heterocycles 2004, 63, 903-974; d) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199-9223; e) P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225-9283; for information from the internet, see: f) http://www.maos.net.
7. For monographs, see: a) B. L. Hayes, Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, NC, 2002; b) A. Loupy (Ed.), Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, 2002; for recent reviews, see: c) Y. Xu, Q.-X. Guo, Heterocycles 2004, 63, 903-974; d) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199-9223; e) P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225-9283; for information from the internet, see: f) http://www.maos.net.
8. For monographs, see: a) B. L. Hayes, Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, NC, 2002; b) A. Loupy (Ed.), Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, 2002; for recent reviews, see: c) Y. Xu, Q.-X. Guo, Heterocycles 2004, 63, 903-974; d) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199-9223; e) P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225-9283; for information from the internet, see: f) http://www.maos.net.
9. For monographs, see: a) B. L. Hayes, Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, NC, 2002; b) A. Loupy (Ed.), Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, 2002; for recent reviews, see: c) Y. Xu, Q.-X. Guo, Heterocycles 2004, 63, 903-974; d) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199-9223; e) P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225-9283; for information from the internet, see: f) http://www.maos.net.
10. For monographs, see: a) B. L. Hayes, Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, NC, 2002; b) A. Loupy (Ed.), Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, 2002; for recent reviews, see: c) Y. Xu, Q.-X. Guo, Heterocycles 2004, 63, 903-974; d) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199-9223; e) P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225-9283; for information from the internet, see: f) http://www.maos.net.
11. For some recent examples, see: a) P. S. Baran, D. P. O'Malley, A. L. Zografos, Angew. Chem. Int. Ed. 2004, 43, 2674-2677; b) M. Shanmugasundaram, S. Manikandan, R. Raghunathan, Tetrahedron 2002, 58, 997-1003; c) J.-B. Daskiewicz, C. Bayet, D. Barron, Tetrahedron Lett. 2001, 42, 7241-7244; d) M. Sridhar, K. L. Krishna, K. Srinivas, J. M. Rao, Tetrahedron Lett. 1998, 39, 6529-6532.
12. For some recent examples, see: a) P. S. Baran, D. P. O'Malley, A. L. Zografos, Angew. Chem. Int. Ed. 2004, 43, 2674-2677; b) M. Shanmugasundaram, S. Manikandan, R. Raghunathan, Tetrahedron 2002, 58, 997-1003; c) J.-B. Daskiewicz, C. Bayet, D. Barron, Tetrahedron Lett. 2001, 42, 7241-7244; d) M. Sridhar, K. L. Krishna, K. Srinivas, J. M. Rao, Tetrahedron Lett. 1998, 39, 6529-6532.
13. For some recent examples, see: a) P. S. Baran, D. P. O'Malley, A. L. Zografos, Angew. Chem. Int. Ed. 2004, 43, 2674-2677; b) M. Shanmugasundaram, S. Manikandan, R. Raghunathan, Tetrahedron 2002, 58, 997-1003; c) J.-B. Daskiewicz, C. Bayet, D. Barron, Tetrahedron Lett. 2001, 42, 7241-7244; d) M. Sridhar, K. L. Krishna, K. Srinivas, J. M. Rao, Tetrahedron Lett. 1998, 39, 6529-6532.
14. For some recent examples, see: a) P. S. Baran, D. P. O'Malley, A. L. Zografos, Angew. Chem. Int. Ed. 2004, 43, 2674-2677; b) M. Shanmugasundaram, S. Manikandan, R. Raghunathan, Tetrahedron 2002, 58, 997-1003; c) J.-B. Daskiewicz, C. Bayet, D. Barron, Tetrahedron Lett. 2001, 42, 7241-7244; d) M. Sridhar, K. L. Krishna, K. Srinivas, J. M. Rao, Tetrahedron Lett. 1998, 39, 6529-6532.
15. a) K. Shiomi, H. Tomoda, K. Otoguro, S. Omura, Pure Appl. Chem. 1999, 71, 1059-1064;
16. b) A. B. Smith III, T. Kinsho, T. Sunazuka, S. Omura, Tetrahedron Lett. 1996, 37, 6461-6464;
17. c) H. Tomoda, N. Tabata, D.-J. Yang, I. Namatame, H. Tanaka, S. Omura, T. Kaneko, J. Antibiot. 1996, 49, 292-298;
18. d) R. Obata, T. Sunazuka, L. Zhuorong, H. Tomoda, S. Omura, J. Antibiot. 1995, 48, 749-750;
19. e) T. Nagamitsu, T. Sunazuka, R. Obata, H. Tomoda, H. Tanaka, Y. Harigaya, S. Omura, A. B. Smith III, J. Org. Chem. 1995, 60, 8126-8127.
20. a) L. F. Tietze, A. Modi, Med. Res. Rev. 2000, 20, 304-322;
21. b) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
22. c) L. F. Tietze, U. Beifuss, Angew. Chem. Int. Ed. 1993, 32, 131-163.
23. Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxy-2H-pyran-2-ones: a) T. Sunazuka, M. Handa, K. Nagai, T. Shirahata, Y. Harigaya, K. Otoguro, I. Kuwajima, S. Omura, Org. Lett. 2002, 4, 367-369; b) D. H. Hua, Y. Chen, H.-S. Sin, M. J. Maroto, P. D. Robinson, S. W. Newell, E. M. Perchellet, J. B. Ladesich, J. A. Freeman, J.-P. Perchellet, P. K. Chiang, J. Org. Chem. 1997, 62, 6888-6896; c) M. Jonassohn, O. Sterner, H. Anke, Tetrahedron 1996, 52, 1473-1478; d) P. de March, M. Moreno-Manas, J. Casado, R. Pleixats, J. L. Roca, A. Trius, J. Heterocycl. Chem. 1984, 21, 85-89; Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxycoumarins: e) Y. R. Lee, D. H. Kim, J.-J. Shim, S. K. Kim, J. H. Park, J. S. Cha, C.-S. Lee, Bull. Korean Chem. Soc. 2002, 23, 998-1002; f) G. Appendino, G. Cravotto, G. B. Giovenzana, G. Palmisano, J. Nat. Prod. 1999, 62, 1627-1631; g) G. Appendino, G. Cravotto, S. Tagliapietra, G. M. Nano, G. Palmisano, Helv. Chim. Acta 1990, 73, 1865-1878; h) G. Appendino, S. Tagliapietra, G. M. Nano, V. Picci, Phytochemistry 1988, 27, 944-946.
24. Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxy-2H-pyran-2-ones: a) T. Sunazuka, M. Handa, K. Nagai, T. Shirahata, Y. Harigaya, K. Otoguro, I. Kuwajima, S. Omura, Org. Lett. 2002, 4, 367-369; b) D. H. Hua, Y. Chen, H.-S. Sin, M. J. Maroto, P. D. Robinson, S. W. Newell, E. M. Perchellet, J. B. Ladesich, J. A. Freeman, J.-P. Perchellet, P. K. Chiang, J. Org. Chem. 1997, 62, 6888-6896; c) M. Jonassohn, O. Sterner, H. Anke, Tetrahedron 1996, 52, 1473-1478; d) P. de March, M. Moreno-Manas, J. Casado, R. Pleixats, J. L. Roca, A. Trius, J. Heterocycl. Chem. 1984, 21, 85-89; Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxycoumarins: e) Y. R. Lee, D. H. Kim, J.-J. Shim, S. K. Kim, J. H. Park, J. S. Cha, C.-S. Lee, Bull. Korean Chem. Soc. 2002, 23, 998-1002; f) G. Appendino, G. Cravotto, G. B. Giovenzana, G. Palmisano, J. Nat. Prod. 1999, 62, 1627-1631; g) G. Appendino, G. Cravotto, S. Tagliapietra, G. M. Nano, G. Palmisano, Helv. Chim. Acta 1990, 73, 1865-1878; h) G. Appendino, S. Tagliapietra, G. M. Nano, V. Picci, Phytochemistry 1988, 27, 944-946.
25. Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxy-2H-pyran-2-ones: a) T. Sunazuka, M. Handa, K. Nagai, T. Shirahata, Y. Harigaya, K. Otoguro, I. Kuwajima, S. Omura, Org. Lett. 2002, 4, 367-369; b) D. H. Hua, Y. Chen, H.-S. Sin, M. J. Maroto, P. D. Robinson, S. W. Newell, E. M. Perchellet, J. B. Ladesich, J. A. Freeman, J.-P. Perchellet, P. K. Chiang, J. Org. Chem. 1997, 62, 6888-6896; c) M. Jonassohn, O. Sterner, H. Anke, Tetrahedron 1996, 52, 1473-1478; d) P. de March, M. Moreno-Manas, J. Casado, R. Pleixats, J. L. Roca, A. Trius, J. Heterocycl. Chem. 1984, 21, 85-89; Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxycoumarins: e) Y. R. Lee, D. H. Kim, J.-J. Shim, S. K. Kim, J. H. Park, J. S. Cha, C.-S. Lee, Bull. Korean Chem. Soc. 2002, 23, 998-1002; f) G. Appendino, G. Cravotto, G. B. Giovenzana, G. Palmisano, J. Nat. Prod. 1999, 62, 1627-1631; g) G. Appendino, G. Cravotto, S. Tagliapietra, G. M. Nano, G. Palmisano, Helv. Chim. Acta 1990, 73, 1865-1878; h) G. Appendino, S. Tagliapietra, G. M. Nano, V. Picci, Phytochemistry 1988, 27, 944-946.
26. Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxy-2H-pyran-2-ones: a) T. Sunazuka, M. Handa, K. Nagai, T. Shirahata, Y. Harigaya, K. Otoguro, I. Kuwajima, S. Omura, Org. Lett. 2002, 4, 367-369; b) D. H. Hua, Y. Chen, H.-S. Sin, M. J. Maroto, P. D. Robinson, S. W. Newell, E. M. Perchellet, J. B. Ladesich, J. A. Freeman, J.-P. Perchellet, P. K. Chiang, J. Org. Chem. 1997, 62, 6888-6896; c) M. Jonassohn, O. Sterner, H. Anke, Tetrahedron 1996, 52, 1473-1478; d) P. de March, M. Moreno-Manas, J. Casado, R. Pleixats, J. L. Roca, A. Trius, J. Heterocycl. Chem. 1984, 21, 85-89; Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxycoumarins: e) Y. R. Lee, D. H. Kim, J.-J. Shim, S. K. Kim, J. H. Park, J. S. Cha, C.-S. Lee, Bull. Korean Chem. Soc. 2002, 23, 998-1002; f) G. Appendino, G. Cravotto, G. B. Giovenzana, G. Palmisano, J. Nat. Prod. 1999, 62, 1627-1631; g) G. Appendino, G. Cravotto, S. Tagliapietra, G. M. Nano, G. Palmisano, Helv. Chim. Acta 1990, 73, 1865-1878; h) G. Appendino, S. Tagliapietra, G. M. Nano, V. Picci, Phytochemistry 1988, 27, 944-946.
27. Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxy-2H-pyran-2-ones: a) T. Sunazuka, M. Handa, K. Nagai, T. Shirahata, Y. Harigaya, K. Otoguro, I. Kuwajima, S. Omura, Org. Lett. 2002, 4, 367-369; b) D. H. Hua, Y. Chen, H.-S. Sin, M. J. Maroto, P. D. Robinson, S. W. Newell, E. M. Perchellet, J. B. Ladesich, J. A. Freeman, J.-P. Perchellet, P. K. Chiang, J. Org. Chem. 1997, 62, 6888-6896; c) M. Jonassohn, O. Sterner, H. Anke, Tetrahedron 1996, 52, 1473-1478; d) P. de March, M. Moreno-Manas, J. Casado, R. Pleixats, J. L. Roca, A. Trius, J. Heterocycl. Chem. 1984, 21, 85-89; Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxycoumarins: e) Y. R. Lee, D. H. Kim, J.-J. Shim, S. K. Kim, J. H. Park, J. S. Cha, C.-S. Lee, Bull. Korean Chem. Soc. 2002, 23, 998-1002; f) G. Appendino, G. Cravotto, G. B. Giovenzana, G. Palmisano, J. Nat. Prod. 1999, 62, 1627-1631; g) G. Appendino, G. Cravotto, S. Tagliapietra, G. M. Nano, G. Palmisano, Helv. Chim. Acta 1990, 73, 1865-1878; h) G. Appendino, S. Tagliapietra, G. M. Nano, V. Picci, Phytochemistry 1988, 27, 944-946.
28. Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxy-2H-pyran-2-ones: a) T. Sunazuka, M. Handa, K. Nagai, T. Shirahata, Y. Harigaya, K. Otoguro, I. Kuwajima, S. Omura, Org. Lett. 2002, 4, 367-369; b) D. H. Hua, Y. Chen, H.-S. Sin, M. J. Maroto, P. D. Robinson, S. W. Newell, E. M. Perchellet, J. B. Ladesich, J. A. Freeman, J.-P. Perchellet, P. K. Chiang, J. Org. Chem. 1997, 62, 6888-6896; c) M. Jonassohn, O. Sterner, H. Anke, Tetrahedron 1996, 52, 1473-1478; d) P. de March, M. Moreno-Manas, J. Casado, R. Pleixats, J. L. Roca, A. Trius, J. Heterocycl. Chem. 1984, 21, 85-89; Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxycoumarins: e) Y. R. Lee, D. H. Kim, J.-J. Shim, S. K. Kim, J. H. Park, J. S. Cha, C.-S. Lee, Bull. Korean Chem. Soc. 2002, 23, 998-1002; f) G. Appendino, G. Cravotto, G. B. Giovenzana, G. Palmisano, J. Nat. Prod. 1999, 62, 1627-1631; g) G. Appendino, G. Cravotto, S. Tagliapietra, G. M. Nano, G. Palmisano, Helv. Chim. Acta 1990, 73, 1865-1878; h) G. Appendino, S. Tagliapietra, G. M. Nano, V. Picci, Phytochemistry 1988, 27, 944-946.
29. Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxy-2H-pyran-2-ones: a) T. Sunazuka, M. Handa, K. Nagai, T. Shirahata, Y. Harigaya, K. Otoguro, I. Kuwajima, S. Omura, Org. Lett. 2002, 4, 367-369; b) D. H. Hua, Y. Chen, H.-S. Sin, M. J. Maroto, P. D. Robinson, S. W. Newell, E. M. Perchellet, J. B. Ladesich, J. A. Freeman, J.-P. Perchellet, P. K. Chiang, J. Org. Chem. 1997, 62, 6888-6896; c) M. Jonassohn, O. Sterner, H. Anke, Tetrahedron 1996, 52, 1473-1478; d) P. de March, M. Moreno-Manas, J. Casado, R. Pleixats, J. L. Roca, A. Trius, J. Heterocycl. Chem. 1984, 21, 85-89; Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxycoumarins: e) Y. R. Lee, D. H. Kim, J.-J. Shim, S. K. Kim, J. H. Park, J. S. Cha, C.-S. Lee, Bull. Korean Chem. Soc. 2002, 23, 998-1002; f) G. Appendino, G. Cravotto, G. B. Giovenzana, G. Palmisano, J. Nat. Prod. 1999, 62, 1627-1631; g) G. Appendino, G. Cravotto, S. Tagliapietra, G. M. Nano, G. Palmisano, Helv. Chim. Acta 1990, 73, 1865-1878; h) G. Appendino, S. Tagliapietra, G. M. Nano, V. Picci, Phytochemistry 1988, 27, 944-946.
30. Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxy-2H-pyran-2-ones: a) T. Sunazuka, M. Handa, K. Nagai, T. Shirahata, Y. Harigaya, K. Otoguro, I. Kuwajima, S. Omura, Org. Lett. 2002, 4, 367-369; b) D. H. Hua, Y. Chen, H.-S. Sin, M. J. Maroto, P. D. Robinson, S. W. Newell, E. M. Perchellet, J. B. Ladesich, J. A. Freeman, J.-P. Perchellet, P. K. Chiang, J. Org. Chem. 1997, 62, 6888-6896; c) M. Jonassohn, O. Sterner, H. Anke, Tetrahedron 1996, 52, 1473-1478; d) P. de March, M. Moreno-Manas, J. Casado, R. Pleixats, J. L. Roca, A. Trius, J. Heterocycl. Chem. 1984, 21, 85-89; Domino Knoevenagel condensation/6π-electron electrocyclization reactions of α,β-unsaturated aldehydes with substituted 4-hydroxycoumarins: e) Y. R. Lee, D. H. Kim, J.-J. Shim, S. K. Kim, J. H. Park, J. S. Cha, C.-S. Lee, Bull. Korean Chem. Soc. 2002, 23, 998-1002; f) G. Appendino, G. Cravotto, G. B. Giovenzana, G. Palmisano, J. Nat. Prod. 1999, 62, 1627-1631; g) G. Appendino, G. Cravotto, S. Tagliapietra, G. M. Nano, G. Palmisano, Helv. Chim. Acta 1990, 73, 1865-1878; h) G. Appendino, S. Tagliapietra, G. M. Nano, V. Picci, Phytochemistry 1988, 27, 944-946.
31. For reviews, see: a) L. F. Tietze, U. Beifuss, The Knoevenagel Reaction, in: B. M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, pp. 341-394; b) G. Jones, Org. React. 1967, 15, 204-599.
32. For reviews, see: a) L. F. Tietze, U. Beifuss, The Knoevenagel Reaction, in: B. M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, pp. 341-394; b) G. Jones, Org. React. 1967, 15, 204-599.
33. For 6π-electron electrocyclization reactions involving 1-oxatrienes, see: a) A. V. Kurdyumov, R. P. Hsung, K. Ihlen, J. Wang, Org. Lett. 2003, 5, 3935-3938; b) K. A. Parker, T. L. Mindt, Org. Lett. 2001, 3, 3875-3878; c) K. Shishido, K. Hiroya, K. Fukumoto, T. Kametani, Tetrahedron Lett. 1986, 27, 971-974; d) K. Shishido, E. Shitara, K. Fukumoto, T. Kametani, J. Am. Chem. Soc. 1985, 107, 5810-5812; e) K. Shishido, M. Ito, S.-I. Shimada, K. Fukumoto, T. Kametani, Chem. Lett. 1984, 1943-1946; f) T. Kametani, M. Kajiwara, K. Fukumoto, Tetrahedron 1974, 30, 1053-1058.
34. For 6π-electron electrocyclization reactions involving 1-oxatrienes, see: a) A. V. Kurdyumov, R. P. Hsung, K. Ihlen, J. Wang, Org. Lett. 2003, 5, 3935-3938; b) K. A. Parker, T. L. Mindt, Org. Lett. 2001, 3, 3875-3878; c) K. Shishido, K. Hiroya, K. Fukumoto, T. Kametani, Tetrahedron Lett. 1986, 27, 971-974; d) K. Shishido, E. Shitara, K. Fukumoto, T. Kametani, J. Am. Chem. Soc. 1985, 107, 5810-5812; e) K. Shishido, M. Ito, S.-I. Shimada, K. Fukumoto, T. Kametani, Chem. Lett. 1984, 1943-1946; f) T. Kametani, M. Kajiwara, K. Fukumoto, Tetrahedron 1974, 30, 1053-1058.
35. For 6π-electron electrocyclization reactions involving 1-oxatrienes, see: a) A. V. Kurdyumov, R. P. Hsung, K. Ihlen, J. Wang, Org. Lett. 2003, 5, 3935-3938; b) K. A. Parker, T. L. Mindt, Org. Lett. 2001, 3, 3875-3878; c) K. Shishido, K. Hiroya, K. Fukumoto, T. Kametani, Tetrahedron Lett. 1986, 27, 971-974; d) K. Shishido, E. Shitara, K. Fukumoto, T. Kametani, J. Am. Chem. Soc. 1985, 107, 5810-5812; e) K. Shishido, M. Ito, S.-I. Shimada, K. Fukumoto, T. Kametani, Chem. Lett. 1984, 1943-1946; f) T. Kametani, M. Kajiwara, K. Fukumoto, Tetrahedron 1974, 30, 1053-1058.
36. For 6π-electron electrocyclization reactions involving 1-oxatrienes, see: a) A. V. Kurdyumov, R. P. Hsung, K. Ihlen, J. Wang, Org. Lett. 2003, 5, 3935-3938; b) K. A. Parker, T. L. Mindt, Org. Lett. 2001, 3, 3875-3878; c) K. Shishido, K. Hiroya, K. Fukumoto, T. Kametani, Tetrahedron Lett. 1986, 27, 971-974; d) K. Shishido, E. Shitara, K. Fukumoto, T. Kametani, J. Am. Chem. Soc. 1985, 107, 5810-5812; e) K. Shishido, M. Ito, S.-I. Shimada, K. Fukumoto, T. Kametani, Chem. Lett. 1984, 1943-1946; f) T. Kametani, M. Kajiwara, K. Fukumoto, Tetrahedron 1974, 30, 1053-1058.
37. For 6π-electron electrocyclization reactions involving 1-oxatrienes, see: a) A. V. Kurdyumov, R. P. Hsung, K. Ihlen, J. Wang, Org. Lett. 2003, 5, 3935-3938; b) K. A. Parker, T. L. Mindt, Org. Lett. 2001, 3, 3875-3878; c) K. Shishido, K. Hiroya, K. Fukumoto, T. Kametani, Tetrahedron Lett. 1986, 27, 971-974; d) K. Shishido, E. Shitara, K. Fukumoto, T. Kametani, J. Am. Chem. Soc. 1985, 107, 5810-5812; e) K. Shishido, M. Ito, S.-I. Shimada, K. Fukumoto, T. Kametani, Chem. Lett. 1984, 1943-1946; f) T. Kametani, M. Kajiwara, K. Fukumoto, Tetrahedron 1974, 30, 1053-1058.
38. For 6π-electron electrocyclization reactions involving 1-oxatrienes, see: a) A. V. Kurdyumov, R. P. Hsung, K. Ihlen, J. Wang, Org. Lett. 2003, 5, 3935-3938; b) K. A. Parker, T. L. Mindt, Org. Lett. 2001, 3, 3875-3878; c) K. Shishido, K. Hiroya, K. Fukumoto, T. Kametani, Tetrahedron Lett. 1986, 27, 971-974; d) K. Shishido, E. Shitara, K. Fukumoto, T. Kametani, J. Am. Chem. Soc. 1985, 107, 5810-5812; e) K. Shishido, M. Ito, S.-I. Shimada, K. Fukumoto, T. Kametani, Chem. Lett. 1984, 1943-1946; f) T. Kametani, M. Kajiwara, K. Fukumoto, Tetrahedron 1974, 30, 1053-1058.
39. a) H. C. Shen, J. Wang, K. P. Cole, M. J. McLaughlin, C. D. Morgan, C. J. Douglas, R. P. Hsung, H. A. Coverdale, A. I. Gerasyuto, J. M. Hahn, J. Liu, H. M. Sklenicka, L.-L. Wei, L. R. Zehnder, C. A. Zificsak, J. Org. Chem. 2003, 68, 1729-1735;
40. b) M. J. McLaughlin H. C. Shen, R. P. Hsung, Tetrahedron Lett. 2001, 42, 609-613;
41. c) R. P. Hsung, H. C. Shen, C. J. Douglas, C. D. Morgan, S. J. Degen, L. J. Yao, J. Org. Chem. 1999, 64, 690-691;
42. d) G. Cravotto, G. M. Nano, S. Tagliapietra, Synthesis 2001, 49-51.
43. a) H. Leutbecher, unpublished results;
44. b) S. Rieg, unpublished results.