Reactivity of allenylphosphonates toward salicylaldehydes and activated phenols: Facile synthesis of chromenes and substituted butadienes

Journal of Organic Chemistry

Volumn 74, Issue 15, 2009, Pages 5395-5404

  Bhuvan Kumar, N N ^a   Nagarjuna Reddy, M ^a   Kumara Swamy, K C ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION PRODUCTS; ALLENYLPHOSPHONATE; CHEMICAL EQUATIONS; CHROMENES; FACILE SYNTHESIS; GOOD YIELD; HORNER-WADSWORTH-EMMONS REACTION; INTERCONVERSION; NMR SPECTROSCOPY; ORGANOCATALYST; P-C BOND CLEAVAGE; PEG-400; PHOSPHONATES; REACTION CONDITIONS; SALICYL ALDEHYDE; SINGLE CRYSTAL X-RAY CRYSTALLOGRAPHY; THEORETICAL CALCULATIONS;

BUTADIENE; CHEMICAL BONDS; CHEMICAL REACTIONS; DIMETHYL SULFOXIDE; ETHERS; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; POLYETHYLENE GLYCOLS; X RAY CRYSTALLOGRAPHY;

PHENOLS;

1,3 BUTADIENE DERIVATIVE; 2 HYDROXY ACETOPHENONE DERIVATIVE; ALLENYLPHOSPHONATE DERIVATIVE; BENZOPHENONE DERIVATIVE; CHROMENE DERIVATIVE; DIMETHYL SULFOXIDE; ETHER DERIVATIVE; MACROGOL 400; PHENOL DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; HORNER WADSWORTH EMMONS REACTION; ISOMER; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; BENZOPYRANS; BUTADIENES; MOLECULAR STRUCTURE; PHENOLS; PHOSPHONIC ACIDS; STEREOISOMERISM;

EID: 68049101356     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900896v     Document Type: Article

References (95)

1. Selected recent reviews: (a) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12.
2. (b) Wei, Lin-Li; Xiong, H.; Hsung, R. P. Acc. Chem. Res. 2003, 36, 773.
3. (c) Ma, S. Acc. Chem. Res. 2003, 36, 773.
4. (d) Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196.
5. (e) Ma, S. Chem. Rev. 2005, 105, 2829.
6. (f) Ma, S. Pure Appl. Chem. 2006, 78, 197.
7. (g) Hassan, H. H. A. M. Current Organic Synthesis 2007, 4, 413.
8. (h) Kim, H.; Williams, L. J Curr. Opin. Drug Discovery Dev. 2008, 11, 870.
9. (i) Zeni, G.; Larock, R. C. Chem. Rev. 2007, 107, 303.
10. Some recent references (2008): (a) Guo, H.; Qian, R.; Guo, Y.; Ma, S. J. Org. Chem. 2008, 73, 7934.
11. (b) Nishina, N.; Yamamoto, Y. Tetrahedron Lett. 2008, 49, 4908.
12. (c) Creech, G. S.; Zhu, X.-F.; Fonovic, B.; Dudding, T.; Kwon, O. Tetrahedron 2008, 64, 6935.
13. (d) Tsukamoto, H.; Kondo, Y. Org. Lett. 2008, 10, 2633.
14. (e) Chen, B.; Lu, Z.; Chai, G.; Fu, C.; Ma, S. J. Org. Chem. 2008, 73, 9486.
15. (f) Lian, X.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 8255.
16. (g) Cheng, X.; Jiang, X.; Yu, Y.; Ma, S. J. Org. Chem. 2008, 73, 8960.
17. (h) Huang, X.; Sha, F. J. Org. Chem. 2008, 73, 1173.
18. (i) Kim, S.; Lee, P. H. Eur. J. Org. Chem. 2008, 2262.
19. (j) Li, W.; Shi, M. J. Org. Chem. 2008, 73, 6698.
20. (k) Shi, M.; Tang, X.-Y.; Yang, Y.-H. J. Org. Chem. 2008, 73, 5311.
21. (l) Alcaide, B.; Almendros, P.; Campo, T. M.; Carrascosa, R. Chem. - Asian J. 2008, 3, 1140.
22. (m) Brummond, K. M.; Chen, D.; Davis, M. M. J. Org. Chem. 2008, 73, 5064.
23. (n) Kitagaki, S.; Kawamura, T.; Shibata, D.; Mukai, C. Tetrahedron 2008, 64, 11086.
24. (o) Liu, L.-P.; Xu, B.; Mashuta, M. S.; Hammond, G. B. J. Am. Chem. Soc. 2008, 130, 17642.
25. (p) Miura, T.; Ueda, K.; Takahashi, Y.; Murakami, M. Chem. Commun. 2008, 5366.
26. (q) Bolano, T.; Castarlenas, R.; Esteruelas, M. A.; Onate, E. Organometallics 2008, 27, 6367.
27. (r) Tsukamoto, H.; Kondo, Y. Angew. Chem., Int. Ed. 2008, 47, 4851.
28. (s) Creech, G. S.; Kwon, O. Org. Lett. 2008, 10, 429.
29. (t) Feldman, K. S.; Iyer, M. R.; Lopez, C. S.; Faza, O. N. J. Org. Chem. 2008, 73, 5090.
30. (u) Tsukamoto, H.; Kondo, Y. Org. Lett. 2008, 10, 2633.
31. (v) Daini, M.; Yoshikawa, M.; Inada, Y.; Uemura, S.; Sakata, K.; Kanao, K.; Miyake, Y.; Nishibayashi, Y. Organometallics 2008, 27, 2046.
32. (w) Castarlenas, R.; Esteruelas, M. A.; Lalrempuia, R.; Olivan, M.; Onate, E. Organometallics 2008, 27, 795.
33. Biological activity: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196.
34. (b) Krause, N., Hashmi, A. S. K., Eds.; Modern Allene Chemistry; Wiley-VCH: Weinheim, 2004.
35. Nixon, N. S.; Scheinmann, F. Tetrahedron Lett. 1983, 24, 597.
36. (a) Shi, Y.-L.; Shi, M. Org. Lett. 2005, 7, 3057.
37. (b) Zhao, G.-L.; Shi, Y.-L.; Shi, M. Org. Lett. 2005, 7, 4527.
38. (c) Shi, M.; Dai, L.-Z.; Shi, Y.-L.; Zhao, G.-L. Adv. Synth. Catal. 2006, 348, 967.
39. (d) Dai, L.-Z.; Shi, Y.-L.; Zhao, G.-L.; Shi, M. Chem.-Eur. J. 2007, 13, 3701.
40. (e) Shi, Y.-L.; Shi, M. Org. Biomol. Chem. 2007, 5, 1499.
41. (a) Liu, K.; Chougnet, A.; Woggon, W.-D. Angew. Chem., Int. Ed. 2008, 47, 1.
42. (b) Lee, Y. R.; Choi, J. H.; Yoon, S. H. Tetrahedron Lett. 2005, 46, 7539.
43. (c) Lee, Y. R.; Wang, X. Org. Biomol. Chem. 2005, 3, 3955.
44. (d) Cueva, J. P.; Giorgioni, G.; Grubbs, R. A.; Chemel, B. R.; Watts, V. J.; Nichols, D. E. J. Med. Chem. 2006, 49, 6848.
45. (e) Kemnitzer, W.; Drewe, J.; Jiang, S.; Zhang, H.; Crogan-Grundy, C.; Labreque, D.; Bubenick, M.; Attardo, G.; Denis, R.; Lamothe, S.; Gourdeau, H.; Tseng, B.; Kasibhatla, S.; Cai, S. X. J. Med. Chem. 2008, 51, 417.
46. (f) Bulman Page, P. C.; Buckley, B. R.; Heaney, H.; Blacker, A. J. Org. Lett. 2005, 7, 375.
47. (g) Liu, F.; Evans, T.; Das, B. C. Tetrahedron Lett. 2008, 49, 1578.
48. (a) Alabugin, I. V.; Brei, V. K. Russ. Chem. Rev. 1997, 66, 205.
49. (b) Zapata, A. J.; Gu, Y.; Hammond, G. B. J. Org. Chem. 2000, 65, 227.
50. (c) Zhao, C. Q.; Han, L. B.; Tanaka, M. Organometallics 2000, 19, 4196.
51. (d) Rubin, M.; Markov, J.; Chuprakov, S.; Wink, D. J.; Gevorgyan, V. J. Org. Chem. 2003, 68, 6251.
52. (e) Nishimura, T.; Hirabayashi, S.; Hayashi, T. J. Am. Chem. Soc. 2006, 126, 2556.
53. (f) Ma, S.; Guo, H.; Yu, F. J. Org. Chem. 2006, 71, 6634.
54. (g) Chakravarty, M.; Kumara Swamy, K. C. J. Org. Chem. 2006, 71, 9128.
55. (h) Kumara Swamy, K. C.; Balaraman, E.; Satish Kumar, N. Tetrahedron 2006, 62, 10152.
56. (i) Chakravarty, M.; Kumara Swamy, K. C. Synthesis 2007, 3171.
57. (j) Yuan, J.; Ruan, X.; Yang, Y.; Huang, X. Synlett 2007, 2871.
58. (k) Chakravarty, M.; Bhuvan Kumar, N. N.; Sajna, K. V.; Kumara Swamy, K. C. Eur. J. Org. Chem. 2008, 4500.
59. (l) Panossian, A.; Fleury-Brégeot, N.; Marinetti, A. Eur. J. Org. Chem. 2008, 3826.
60. (m) de los Santos, J. M.; Lòpez, Y.; Aparicio, D.; Palacios, F. J. Org. Chem. 2008, 73, 550.
61. (a) Muthiah, C.; Praveen Kumar, K.; Aruna Mani, C.; Kumara Swamy, K. C. J. Org. Chem. 2000, 65, 3733.
62. (b) Praveen Kumar, K.; Muthiah, C.; Kumaraswamy, S.; Kumara Swamy, K. C. Tetrahedron Lett. 2001, 42, 3219.
63. (c) Muthiah, C.; Senthil Kumar, K.; Vittal, J. J.; Kumara Swamy, K. C. Synlett 2002, 1787.
64. (d) Chakravarty, M.; Srinivas, B.; Muthiah, C.; Kumara Swamy, K. C. Synthesis 2003, 2368.
65. (e) Kumara Swamy, K. C.; Kumaraswamy, S.; Senthil Kumar, K.; Muthiah, C. Tetrahedron Lett. 2005, 46, 3347.
66. (f) Kumara Swamy, K. C.; Pavan Kumar, K. V. P.; Rama Suresh, R.; Satish Kumar, N. Synthesis 2007, 1485.
67. (g) Kumara Swamy, K. C.; Srinivas, V.; Pavan Kumar, K. V. P.; Praveen Kumar, K. Synthesis 2007, 893.
68. Selected references on the utility of organophosphonates: (a) Iorga, B.; Eymery, F.; Savignac, P. Synthesis 2000, 576.
69. (b) Tago, K.; Kogen, H. Org. Lett. 2000, 2, 1975.
70. (c) Sun, S.; Turchi, I. J.; Xu, D.; Murray, W. V. J. Org. Chem. 2000, 65, 2555.
71. (d) Vaes, L.; Rein, T. Org. Lett. 2000, 2, 2611.
72. (e) Reiser, U.; Jauch, J. Synlett 2001, 90.
73. (f) Crist, R. M.; Reddy, P. V.; Borhan, B. Tetrahedron Lett. 2001, 42, 619.
74. (g) Kawasaki, T.; Nonaka, Y.; Watanabe, K.; Ogawa, A.; Higuchi, K.; Terashima, R.; Masuda, K.; Sakamoto, M. J. Org. Chem. 2001, 66, 1200.
75. (h) Gelman, D.; Jiang, L.; Buchwald, S. L. Org. Lett. 2003, 5, 2315.
76. (i) Pamies, O.; Bäckvall, J.-E. J. Org. Chem. 2003, 68, 4815.
77. (j) Janecki, T.; Wa̧sek, T. Tetrahedron 2004, 60, 1049.
78. (k) Davis, F. A.; Xu, H.; Zhang, J. J. Org. Chem. 2007, 72, 2046.
79. (l) Sulzer-Mosse, S.; Tissot, M.; Alexakis, A. Org. Lett. 2007, 9, 3749.
80. (m) Muruganantham, R.; Mobin, S. M.; Namboothiri, I. N. N. Org. Lett. 2007, 9, 1125.
81. (n) Liu, J.; Yang, Z.; Wang, Z.; Wang, F.; Chen, X.; Liu, X.; Feng, X.; Su, Z.; Hu, C. J. Am. Chem. Soc. 2008, 130, 5654.
82. (a) Corbridge, D. E. C. Phosphorus 2000-Chemistry, Biochemistry and Technology; Elsevier: Amsterdam, 2000.
83. (b) Kukhar, V. P., Hudson, H. R., Eds.; Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity; John Wiley & Sons: Chichester, U.K., 2000.
84. (c) Savignac, P.; Iorga, B. Modern Phosphonate Chemistry; CRC Press, Boca Raton, 2003.
85. (d) Palacios, F.; Alonso, C.; de los Santos, J. M. Chem. Rev. 2005, 105, 899.
86. Bhuvan Kumar, N. N.; Chakravarty, M.; Satish Kumar, N.; Sajna, K. V.; Kumara Swamy, K. C. J. Chem. Sci. 2009, 121, 23.
87. In the reactions using 5-chlorosalicylaldehyde and 2-hydroxy acetophenone, although reaction mixture showed products similar to 19 as the major components, we were able to isolate only the chromenes I and II, probably because of the ease of dehydration. (Chemical Equation Presented)
88. McClelland, R. A.; Gedge, S. J. Am. Chem. Soc. 1980, 102, 5839.
89. (a) Finkelstein, B. L.; Benner, E. A.; Hendrixson, M. C.; Kranis, K. T.; Rauh, J. J.; Sethuraman, M. R.; McCann, S. F. Bioorg. Med. Chem. 2002, 10, 599.
90. (b) Kawai, Y.; Hayashi, M.; Tokitoh, N. Tetrahedron: Asymmetry 2001, 12, 3007.
91. A small quantity of (Z)-chromenol (III) could also be isolated from the reaction performed at the lower temperature of 80°C using 9d, salicylaldehyde, and DBU as the base. At higher temperatures we could not detect this compound. (Chemical Equation Presented)
92. 1H NMR δ 1.71 (s, 3H), 1.79 (s, 3H), 6.19 (d, J = 8.0 Hz, 1H), 6.37 (d, J = 8.0 Hz, 1H), 6.75-7.06 (m, 4H)].
93. (a) Zhang, C.; Lu, X. Synlett 1995, 645.
94. (b) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
95. The allenylphosphonate complex IV reacts smoothly with salicylaldehyde in the presence of sodium hydride to give chromene (V) by internal HWE reaction in good yield as a crystalline solid. See: Müller, T. J. J; Ansorge, M. Tetrahedron 1998, 54, 1457. (Chemical Equation Presented)