Synthesis of Substituted Quinolines and Coumarins through a Sequential Vinylic Substitution/Annulation Process

Synlett

Volumn 1996, Issue 6, 1996, Pages 568-570

  Arcadi, Antonio ^a   Cacchi, Sandro ^b   Fabrizi, Giancarlo ^b   Marinelli, Fabio ^a   Pace, Paola ^b  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001820829     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5479     Document Type: Article

References (44)

1. Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236.
2. Cacchi, S. Pure & Appl. Chem. 1990, 62, 713.
3. 10
4. Clark, F.R.S.; Norman, R.O.C.; Thomas, C.B. J. Chem. Soc., Perkin Trans. 1 1975, 121; Murahashi, S.-I.; Hirano, T.; Yano. T. J. Am. Chem. Soc. 1978, 100, 348; Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429; Murahashi, S.-I.; Yano, T. J. Am. Chem. Soc. 1980, 102, 2456; McCrindle, R.; Ferguson, G.; Arsenault, G.J.; McAless, A.J. J. Chem. Soc., Chem. Commun. 1983, 571.
5. Clark, F.R.S.; Norman, R.O.C.; Thomas, C.B. J. Chem. Soc., Perkin Trans. 1 1975, 121; Murahashi, S.-I.; Hirano, T.; Yano. T. J. Am. Chem. Soc. 1978, 100, 348; Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429; Murahashi, S.-I.; Yano, T. J. Am. Chem. Soc. 1980, 102, 2456; McCrindle, R.; Ferguson, G.; Arsenault, G.J.; McAless, A.J. J. Chem. Soc., Chem. Commun. 1983, 571.
6. Clark, F.R.S.; Norman, R.O.C.; Thomas, C.B. J. Chem. Soc., Perkin Trans. 1 1975, 121; Murahashi, S.-I.; Hirano, T.; Yano. T. J. Am. Chem. Soc. 1978, 100, 348; Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429; Murahashi, S.-I.; Yano, T. J. Am. Chem. Soc. 1980, 102, 2456; McCrindle, R.; Ferguson, G.; Arsenault, G.J.; McAless, A.J. J. Chem. Soc., Chem. Commun. 1983, 571.
7. Clark, F.R.S.; Norman, R.O.C.; Thomas, C.B. J. Chem. Soc., Perkin Trans. 1 1975, 121; Murahashi, S.-I.; Hirano, T.; Yano. T. J. Am. Chem. Soc. 1978, 100, 348; Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429; Murahashi, S.-I.; Yano, T. J. Am. Chem. Soc. 1980, 102, 2456; McCrindle, R.; Ferguson, G.; Arsenault, G.J.; McAless, A.J. J. Chem. Soc., Chem. Commun. 1983, 571.
8. Clark, F.R.S.; Norman, R.O.C.; Thomas, C.B. J. Chem. Soc., Perkin Trans. 1 1975, 121; Murahashi, S.-I.; Hirano, T.; Yano. T. J. Am. Chem. Soc. 1978, 100, 348; Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429; Murahashi, S.-I.; Yano, T. J. Am. Chem. Soc. 1980, 102, 2456; McCrindle, R.; Ferguson, G.; Arsenault, G.J.; McAless, A.J. J. Chem. Soc., Chem. Commun. 1983, 571.
9. For the utilization of trialkylamines as reducing agents in palladium-catalysed hydroarylations of cyclic α,β-unsaturated carbonyl compounds see, for example: Stokker, G.E. Tetrahedron Lett. 1987, 28, 3179; Konopelski, J.P.; Chu, K.S.; Negrete, G.R. J. Org. Chem. 1991, 56, 1355; Friestad, G.K.; Branchaud, B.P. Tetrahedron Lett. 1995, 36, 7047.
10. For the utilization of trialkylamines as reducing agents in palladium-catalysed hydroarylations of cyclic α,β-unsaturated carbonyl compounds see, for example: Stokker, G.E. Tetrahedron Lett. 1987, 28, 3179; Konopelski, J.P.; Chu, K.S.; Negrete, G.R. J. Org. Chem. 1991, 56, 1355; Friestad, G.K.; Branchaud, B.P. Tetrahedron Lett. 1995, 36, 7047.
11. For the utilization of trialkylamines as reducing agents in palladium-catalysed hydroarylations of cyclic α,β-unsaturated carbonyl compounds see, for example: Stokker, G.E. Tetrahedron Lett. 1987, 28, 3179; Konopelski, J.P.; Chu, K.S.; Negrete, G.R. J. Org. Chem. 1991, 56, 1355; Friestad, G.K.; Branchaud, B.P. Tetrahedron Lett. 1995, 36, 7047.
12. For examples of reduction of o-arylpalladium complexes by trialkylamines, see: Saá, J.M.; Dopico, M.; Martorell, G.; Garcia-Raso, A. J. Org. Chem. 1990, 55, 991; Cabri, W. Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796; Laschat, S.; Narjes, F.; Overman, L.E. Tetrahedron 1994, 50, 347.
13. For examples of reduction of o-arylpalladium complexes by trialkylamines, see: Saá, J.M.; Dopico, M.; Martorell, G.; Garcia-Raso, A. J. Org. Chem. 1990, 55, 991; Cabri, W. Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796; Laschat, S.; Narjes, F.; Overman, L.E. Tetrahedron 1994, 50, 347.
14. For examples of reduction of o-arylpalladium complexes by trialkylamines, see: Saá, J.M.; Dopico, M.; Martorell, G.; Garcia-Raso, A. J. Org. Chem. 1990, 55, 991; Cabri, W. Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796; Laschat, S.; Narjes, F.; Overman, L.E. Tetrahedron 1994, 50, 347.
15. Yamamura, K. J. Org. Chem. 1978, 43, 724.
16. 1
17. For the reactivity of conjugated nitroalkenes, see: Denmark, S.E.; Schnute, M.E. J. Org. Chem. 1995, 60, 1013.
18. Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813.
19. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron in press.
20. +, 11), 146 (100), 118 (52).
21. 4NCl (0.75 h), and KOAc (2 h) compound 2 was isolated in 38,41, and 63% yield, respectively (DMF, 60 °C).
22. Burini, A.; Cacchi, S.; Pace, P.; Pietroni, B. R. Synlett 1995, 677.
23. The regiochemistry of substituted quinolines and coumarins was determined by NOE experiments. As an example, the relevant NOE effects for the regioisomeric quinoline derivatives obtained from the reaction of 3,3,5,5-tetramethylcyclohex-1-enyl triflate with 4 are as follows: (Matrix Presented)
24. +, 72), 264 (100).
25. Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287.
26. Jeffery, T. Tetrahedron Lett. 1985, 26, 2667.
27. 4
28. The preparation of 4-substituted-coumarins 10 has been performed at 80 °C according to the procedure described in ref. 16.
29. For reviews on the synthesis of quinolines, see: Jones, G. Chem. Heterocycl. Compd. 1977, 32, 93; Cheng, C.-C.; Yan, S.-J. Org. React. 1983, 28, 37.
30. For reviews on the synthesis of quinolines, see: Jones, G. Chem. Heterocycl. Compd. 1977, 32, 93; Cheng, C.-C.; Yan, S.-J. Org. React. 1983, 28, 37.
31. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
32. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
33. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
34. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
35. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
36. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
37. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
38. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
39. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
40. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
41. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
42. For the synthesis of quinoline derivatives based on palladium chemistry, see: Cortese, N.A.; Ziegler, Jr., C.B.; Hrnjez, B.J.; Heck, R.F. J. Org. Chem. 1978, 43, 2952; Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003; Cacchi, S.; Palmieri, G. Tetrahedron 1983, 39, 3373; Yamanaka, H.; Annaka, M.; Koado, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309; Larock, R.C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Negishi, E.; Takahashi, T.; King, A.O. Org. Synth. 1988, 66, 67; Crisp, G.T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279; Larock, R.C.; Kuo, M.-Y. Tetrahedron Lett. 1991, 32, 569; Tori, S.; Xu, L.H.; Sadakane, M.; Okumoto, H. Synlett 1992, 514; Kundu, N.G.; Mahanty, J.S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625; Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 7919.
43. For a review on the synthesis of coumarins, see: Darbarwar, M.; Sundaramurthy, V. Synthesis 1982, 337.
44. For the synthesis of coumarin derivatives based on palladium chemistry, see: Catellani, M.; Chiusoli, G.P.; Fagnola, M.C.; Solari, G. Tetrahedron Lett. 1994, 35, 5919, 5923.