Preparation of 3-acyl-4-arylcoumarins via metal-free tandem oxidative acylation/cyclization between alkynoates with aldehydes

Journal of Organic Chemistry

Volumn 80, Issue 1, 2015, Pages 148-155

  Mi, Xia ^a   Wang, Chenyang ^a   Huang, Mengmeng ^a   Wu, Yusheng ^b   Wu, Yangjie ^a  

^a ZHENGZHOU UNIVERSITY   (China)

^b Tetranov Biopharm LLC   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES;

ACYL RADICALS; ALKYNOATES; C-C BONDS; C-H BOND FUNCTIONALIZATION; METAL FREE;

ACYLATION;

3 (2 HYDROXYLBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (2 METHYLBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (2,4 DICHLOROBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (3 CHLOROBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (3 METHOXYBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (3 METHYLBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (3 METHYLBUTANOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (3,4 DIMETHYLBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (4 BROMOBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (4 CHLOROBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (4 FLUOROBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (4 METHOXYBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (4 METHOXYBENZOYL) 6 METHOXYL 4 PHENYL 2H CHROMEN 2 ONE; 3 (4 METHOXYBENZOYL) 6 METHYL 4 PHENYL 2H CHROMEN 2 ONE; 3 (4 METHOXYBENZOYL) 6 PHENOXYL 4 PHENYL 2H CHROMEN 2 ONE; 3 (4 METHYLBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 (CYCLOPROPANECARBONYL) 4 PHENYL 2H CHROMEN 2 ONE; 3 ACYL 4 ARYLCOUMARIN; 3 BENZOYL 4 PHENYL 2H CHROMEN 2 ONE; 3 BUTYRYL 4 PHENYL 2H CHROMEN 2 ONE; 4 PHENYL 3 (4 TRIFLUOROMETHYLBENZOYL) 2H CHROMEN 2 ONE; 5,7 DIMETHYL 3 (4 METHOXYBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 6 BROMO 3 (4 METHOXYBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 6 CHLORO 3 (4 METHOXYBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 6 FLUORO 3 (4 METHOXYBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; 6 T BUTYL 3 (4 METHOXYBENZOYL) 4 PHENYL 2H CHROMEN 2 ONE; ALDEHYDE; ALKYNE DERIVATIVE; COUMARIN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ALKYNE;

ACYLATION; ARTICLE; CARBON BOND; CHEMICAL BOND; CONTROLLED STUDY; COVALENT BOND; CYCLIZATION; DRUG SYNTHESIS; ELECTRON TRANSPORT; ELECTROSPRAY MASS SPECTROMETRY; METAL FREE TANDEM OXIDATIVE ACYLATION; X RAY ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ACYLATION; ALDEHYDES; ALKYNES; COUMARINS; CYCLIZATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 84928890145     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502220b     Document Type: Article

References (84)

1. Borges, F.; Roleira, F.; Milhazes, N.; Uriarte, E.; Santana, L. Front. Med. Chem. 2009, 4, 23.
2. Goth, A. Science 1945, 101, 383.
3. Eckardt, T.; Hagen, V.; Schade, B.; Schmidt, R.; Schweitzer, C.; Bendig, J. J. Org. Chem. 2002, 67, 703.
4. Wang, C. J.; Hsieh, Y. J.; Chu, C. Y.; Lin, Y. Y.; Tseng, T. H. Cancer Lett. 2002, 183, 163.
5. Zhao, Y.; Zheng, Q.; Dakin, K.; Xu, K.; Martinez, M. L.; Li, W. H. J. Am. Chem. Soc. 2004, 126, 4653.
6. Komatsu, K.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2007, 129, 13447.
7. Signore, G.; Nifosi, R.; Albertazzi, L.; Storti, B.; Bizzarri, R. J. Am. Chem. Soc. 2010, 132, 1276.
8. Wang, C.; Wu, C.; Zhu, J.; Miller, R. H.; Wang, Y. J. Med. Chem. 2011, 54, 2331.
9. Matos, M. J.; Vazquez-Rodriguez, S.; Santana, L.; Uriarte, E.; Fuentes-Edfuf, C.; Santos, Y.; Munoz-Crego, A. Molecules 2013, 18, 1394.
10. Christie, R. M.; Lui, C. H. Dyes Pigm. 2000, 47, 79.
11. Schiedel, M. S.; Briehn, C. A.; Bauerle, P. Angew. Chem., Int. Ed. 2001, 40, 4677.
12. Uchiyama, S.; Takehira, K.; Yoshihara, T.; Tobita, S.; Ohwada, T. Org. Lett. 2006, 8, 5869.
13. Hirano, T.; Hiromoto, K.; Kagechika, H. Org. Lett. 2007, 9, 1315.
14. Turki, H.; Abid, S.; Fery-Forgues, S.; El Gharbi, R. Dyes Pigm. 2007, 73, 311.
15. Sastry, V. D. N.; Seshadri, T. R. Proc. Ind. Acad. Sci. 1942, 16A, 29.
16. Chem. Abstr. 1943, 37, 880.
17. Yamashita, M.; Okuyama, K.; Kawajiri, T.; Takada, A.; Inagaki, Y.; Nakano, H.; Tomiyama, M.; Ohnaka, A.; Teryama, I.; Kawasaki, I.; Ohta, S. Tetrahedron 2002, 58, 1497.
18. Nemeryuk, M. P.; Dimitrova, V. D.; Anisimova, O. S.; Sedov, A. L.; Soloveva, N. P.; Traven, V. F. Chem. Heterocycl. Compd. 2003, 39, 1454.
19. Sandhu, S.; Bansal, Y.; Silakari, O.; Bansal, G. Bioorg. Med. Chem. 2014, 22, 3806.
20. Borges, F.; Roleira, F.; Milhazes, N.; Santana, L.; Uriarte, E. Curr. Med. Chem. 2005, 12, 887.
21. Specht, D.-P.; Martic, P.-A.; Farid, S. Tetrahedron 1982, 38, 1203.
22. Raju, B.-C.; Tiwari, A.-K.; Kumar, J.-K.; Ali, A.-Z.; Agawane, S.-B.; Saidachary, G.; Madhusudana, K. Bioorg. Med. Chem. 2010, 18, 358.
23. Heravi, M.-M.; Poormohammad, N.; Beheshtiha, Y.-S.; Baghernejad, B.; Malakooti, R. Chin. J. Chem. 2009, 27, 968.
24. Heravi, M.-M.; Sadjadi, S.; Oskooie, H.-A.; Shoar, R.-H.; Bamoharram, F.-F. Catal. Commun. 2008, 9, 270.
25. Ranu, B.-C.; Jana, R. Eur. J. Org. Chem. 2006, 3767.
26. Ajania, O. O.; Nwinyi, O. C. J. Heterocycl. Chem. 2010, 47, 179.
27. Tang, X.; Blake, A.-J.; Lewis, W.; Woodward, S. Tetrahedron: Asymmetry 2009, 20, 1881.
28. Surya, P. R. H.; Sivakumar, S. J. Org. Chem. 2006, 71, 8715.
29. Yuan, H.-J.; Wang, M.; Liu, Y.-J.; Liu, Q. Adv. Synth. Catal. 2009, 353, 112.
30. Yuan, H.; Wang, M.; Liu, Y.; Wang, L.; Liu, J.; Liu, Q. Chem.-Eur. J. 2010, 16, 13450.
31. Majumdar, K. C.; Samanta, S.; Ansary, I.; Roy, B. RSC Adv. 2012, 1, 2137.
32. Sun, H.; Zhang, Y.; Guo, F.; Yan, Y.; Wan, C.; Zha, Z.; Wang, Z. Eur. J. Org. Chem. 2012, 480.
33. Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
34. Mcglacken, G. P.; Bateman, L. M.; Bateman, L. Chem. Soc. Rev. 2009, 38, 2447.
35. Shabashov, D. Acc. Chem. Res. 2009, 42, 1074.
36. Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540.
37. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068.
38. Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170.
39. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
40. Xie, Y.-X.; Song, R.-J.; Xiang, J.-N.; Li, J.-H. Chin. J. Org. Chem. 2012, 32, 1555.
41. Pan, C.; Jia, X.; Cheng, J. Synthesis 2012, 44, 677.
42. Tang, B.-X.; Song, R.-J.; Wu, C.-Y.; Liu, Y.; Zhou, M.-B.; Wei, W.-T.; Deng, G.-B.; Yin, D.-L.; Li, J.-H. J. Am. Chem. Soc. 2010, 132, 8900.
43. Jia, X.; Zhang, S.; Wang, W.; Luoand, F.; Cheng, J. Org. Lett. 2009, 11, 3120.
44. Chan, C.-W.; Zhou, Z.; Chan, A. S. C.; Yu, W.-Y. Org. Lett. 2010, 12, 3926.
45. Basle, O.; Bidange, J.; Shuai, Q.; Li, C.-J. Adv. Synth. Catal. 2010, 352, 1145.
46. Wang, P.; Rao, H.; Hua, R.; Li, C.-J. Org. Lett. 2012, 14, 902.
47. Zhou, B.; Yang, Y.; Li, Y. Chem. Commun. 2012, 48, 5163.
48. Park, J.; Park, E.; Kim, A.; Lee, Y.; Chi, K.-W.; Kwak, J.; Jung, Y.; Kim, I. Org. Lett. 2011, 13, 4390.
49. Sharma, S.; Park, E.; Park, J.; Kim, I. Org. Lett. 2012, 14, 906.
50. Li, C.; Wang, L.; Li, P.; Zhou, W. Chem.-Eur. J. 2011, 17, 10208.
51. Shi, Z.; Glorius, F. Chem. Sci. 2013, 4, 829.
52. Chan, C.-W.; Zhou, Z.; Yu, W.-Y. Adv. Synth. Catal. 2011, 353, 2999.
53. Sharma, S.; Park, J.; Park, E.; Kim, A.; Kim, M.; Kwak, J.-H.; Jung, Y.-H.; Kim, I.-S. Adv. Synth. Catal. 2013, 355, 332.
54. Yang, Y.; Zhou, B.; Li, Y. Adv. Synth. Catal. 2012, 354, 2916.
55. Matcha, K.; Antonchick, A.-P. Angew. Chem., Int. Ed. 2013, 52, 2082.
56. Li, X.-A.; Wang, H.-L.; Yang, S.-D. Org. Lett. 2013, 15, 1794.
57. Wertz, S.; Leifert, D.; Studer, A. Org. Lett. 2013, 15, 928.
58. Chudasama, V.; Fitzmaurice, R. J.; Caddick, S. Nat. Chem. 2010, 2, 592.
59. Fitzmaurice, R. J.; Ahern, J.; Caddick, S. Org. Biomol. Chem. 2009, 7, 235.
60. Tsujimoto, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2001, 2352.
61. Tsujimoto, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2003, 44, 5601.
62. Zhou, M.-B.; Song, R.-J.; Ouyang, X.-H.; Liu, Y.; Wei, W.-T.; Deng, G.-B.; Li, J.-H. Chem. Sci. 2013, 4, 2690.
63. Liu, W.; Li, Y.; Liu, K.; Li, Z. J. Am. Chem. Soc. 2011, 133, 10756.
64. Shi, Z.; Schrcder, N.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 8092.
65. Wang, J.; Liu, C.; Yuan, J.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 2256.
66. Bosnich, B. Acc. Chem. Res. 1998, 31, 667.
67. Jun, C.-H.; Hong, J.-B.; Lee, D. L. Synlett 1999, 1.
68. Jun, C.-H.; Jo, E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 1869.
69. Willis, M. C. Chem. Rev. 2010, 110, 725.
70. Gonzalez-Rodriguez, C.; Willis, M. C. Pure Appl. Cem. 2011, 83, 577.
71. Leung, J. C.; Krische, M. J. Chem. Sci. 2012, 3, 2202.
72. Ouyang, K.; Xi, Z. Acta Chim. Sin. 2013, 71, 13.
73. Shirakawa, E.; Hayashi, R. Chem. Lett. 2012, 41, 130.
74. Yanigasawa, S.; Itami, K. Chem. Catal. Chem. 2011, 3, 827.
75. Wang, Y. Synlett. 2011, 2901.
76. Luo, J.-Y.; Hua, H.-L.; Chen, Z.-S.; Zhou, Z.-Z.; Yang, Y.-F.; Zhou, P.-X.; He, Y.-T.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2014, 50, 1564.
77. Ouyang, X.-H.; Song, R.-J.; Li, Y.; Liu, B.; Li, J.-H. J. Org. Chem. 2014, 79, 4582.
78. Mi, X.; Wang, C.; Huang, M.; Zhang, J.; Wu, Y.; Wu, Y. Org. Lett. 2014, 16, 3356.
79. Chen, L.; Shi, E.; Liu, Z.; Chen, S.; Wei, W.; Li, H.; Xu, K.; Wan, X. Chem.-Eur. J. 2011, 17, 4085.
80. Wei, W.; Zhang, C.; Xu, Y.; Wan, X. Chem. Commun. 2011, 47, 10827.
81. Liu, Z.; Zhang, J.; Chen, S.; Shi, E.; Xu, Y.; Wan, X. Angew. Chem., Int. Ed. 2012, 51, 3231.
82. Zhu, X.; Shi, Y.; Mao, H.; Cheng, Y.; Zhu, C. Adv. Synth. Catal. 2013, 355, 3558.
83. Yang, S.-G.; Hwang, J.-P.; Park, M.-Y.; Lee, K.; Kim, Y.-H. Tetrahedron 2007, 63, 5184.
84. Song, C. E.; Jung, D.; Choung, S. Y.; Roh, E. J.; Lee, S. Angew. Chem., Int. Ed. 2004, 43, 6183.