An efficient copper-catalyzed three-component synthesis of 3-C-linked glycosyl iminocoumarins

Synthesis (Germany)

Volumn 44, Issue 12, 2012, Pages 1841-1848

  Palanichamy, Kalanidhi ^a   Suravarapu, Sankar R ^a   Kaliappan, Krishna P ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

alkynes; azides; copper; glycosides; glycosylations; heterocycles; multicomponent reactions

Indexed keywords

ALKYNES; AZIDES; GLYCOSYLATIONS; HETEROCYCLES; MULTI-COMPONENT REACTIONS;

ACETYLENE; ALDEHYDES; CATALYSIS; GLYCOSIDES; REACTION KINETICS; SUGARS;

COPPER;

ALKYNE; AZIDE; COPPER; COUMARIN DERIVATIVE; GLYCOSYL IMINOCOUMARIN DERIVATIVE; N [3 (2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 2H CHROMEN 2 YLDINENE] 4 TOLYLSULFONAMIDE; N [3 (6 METHOXY 2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL) 2H CHROMEN 2 YLIDENE] 4 TOLYLSULFONAMIDE; N [3 [2,2,7,7 TETRAMETHYLTETRAHYDRO 3AH BIS[1,3]DIOXOLO[4,5 B:4',5' D]PYRAN 5 YL] 2H CHROMEN 2 YLIDENE] 4 TOLYL SULFONAMIDE; N [3 [5 [2,2 DIMETHYL 1,3 DIOXOLAN 4 YL] 6 METHOXY 2,2 DIMETHYLTETRAHYDROFURO[2,3 D][1,3]DIOXOL 6 YL] 2H CHROMEN 2 YLIDENE] 4 TOLYLSULFONAMIDE; N [3 [5 [[[TERT BUTYL(DIMETHYL)SILYL]OXY]METHYL] 6 METHOXY 2,2 DIMETHYLTETRAHYDROFURO[2,3 D][1,3]DIOXO 6 YL] 2H CHROMEN 2 YLIDENE] 4 TOLYLSULFONAMIDE; N [3 [6 (BENZYLOXY) 2,2 DIMETHYLTETRAHYDROFURO[2,3 D][1,3]DIOXOL 5 YL] 2H CHROMEN 2 YLIDENE] 4 TOLYLSULFONAMIDE; N [3 [6 [[[TERT BUTYL(DIMETHYL)SILYL]OXY]METHYL] 2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL] 2H CHROMEN 2 YLIDENE] 4 TOYLYSULFONAMIDE; SALICYLALDEHYDE; TOSYL AZIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION;

EID: 84861869374     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289763     Document Type: Article

References (124)

1. Watanabe KA. In The Chemistry of Nucleosides and Nucleotides. Townsend LB. Plenum Press New York: 1994; 421
2. Levy DE, Tang C. The Chemistry of C -Glycosides. Elsevier Oxford: 1995
3. Postema MH. D. C -Glycoside Synthesis. CRC Press Boca Raton: 1995
4. Shaban MA. E, Nasr AZ. Adv. Heterocycl. Chem.: 1997; 68 223
5. Shaban MA. E. Adv. Heterocycl. Chem.: 1997; 70 163
6. Beau JM, Gallagher T. Top. Curr. Chem.: 1997; 187 1
7. Nicotra F. Top. Curr. Chem.: 1997; 187 55
8. Krohn K, Rohr J. Top. Curr. Chem.: 1997; 188 127
9. Du YG, Linhardt RJ, Vlahov IR. Tetrahedron: 1998; 54 9913
10. Dondoni A, Marra A. Chem. Rev.: 2000; 100 4395
11. Somsák L. Chem. Rev.: 2001; 101 81
12. Liu L, McKee M, Postema MH. D. Curr. Org. Chem.: 2001; 5 1133
13. Meo P, Osborn HM. I. In Carbohydrates. Osborn HM. I. Academic Press New York: 2003; Chap. 10 337
14. Lee DY. W, He MS. Curr. Top. Med. Chem.: 2005; 5 1333
15. Yuan X, Linhardt RJ. Curr. Top. Med. Chem.: 2005; 5 1393
16. Lin C.-H, Lin H.-C, Yang W.-B. Curr. Top. Med. Chem.: 2005; 5 1431
17. Adamo MF. A, Pergoli R. Curr. Org. Chem.: 2008; 12 1544
18. Štambask J, Hocek M, Kočovsk P. Chem. Rev.: 2009; 109 6729
19. Findlay JA, Lin J.-S, Radics L, Rachit S. Can. J. Chem.: 1981; 59 3018
20. Sehgel SN, Czerkawski H, Kudelski A, Pander K, Saucier R, Vézina C. J. Antibiot.: 1983; 36 355
21. Daves GD. Jr. Acc. Chem. Res.: 1990; 23 201
22. Postema MH. D. Tetrahedron: 1992; 48 8545
23. Togo H, He W, Waki Y, Yokoyama M. Synlett: 1998; 700
24. Isobe M, Nishizawa R, Hosokawa S, Nishikawa T. Chem. Commun.: 1998; 2665
25. Smoliakova IP. Curr. Org. Chem.: 2000; 4 589
26. Taillefumier C, Chapleur Y. Chem. Rev.: 2004; 104 263
27. Zou W. Curr. Top. Med. Chem.: 2005; 5 1363
28. Saeeng R, Isobe M. Chem. Lett.: 2006; 35 552
29. Compain P, Martin OR. Bioorg. Med. Chem.: 2001; 9 3077
30. Hultin PG. Curr. Top. Med. Chem.: 2005; 5 1299
31. Bililign T, Griffith BR, Thorson JS. Nat. Prod. Rep.: 2005; 22 742
32. Wellington KW, Benner SA. Nucleosides, Nucleotides Nucleic Acids: 2006; 25 1309
33. Murray RD. H, Mendez J, Brown SA. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry. Wiley Chichester: 1982
34. Murray RD. H. Nat. Prod. Rep.: 1995; 12 477
35. O'Kennedy R, Thornes RD. Coumarins: Biology, Applications and Mode of Action. Wiley Chichester: 1997
36. Sardari S, Nishibe S, Daneshtalab M. Stud. Nat. Prod. Chem.: 2000; 23 335
37. Murray RD. H. Prog. Chem. Org. Nat. Prod.: 2002; 83 1
38. Garazd MM, Garazd YL, Khilya VP. Chem. Nat. Compd.: 2003; 39 54
39. Chinchilla R, Nájera C, Yus M. Chem. Rev.: 2004; 104 2667
40. Zhao Y, Zheng Q, Dakin K, Xu K, Martinez ML, Li W.-H. J. Am. Chem. Soc.: 2004; 126 4653
41. Kuo P.-Y, Yang D.-Y. J. Org. Chem.: 2008; 73 6455
42. Musicki B, Periers A.-M, Piombo L, Laurin P, Klich M, Dupuis-Hamelin C, Lassaigne P, Bonnefoy A. Tetrahedron Lett.: 2003; 44 9259
43. Scatigno AC, Garrido SS, Marchetto R. J. Pept. Sci.: 2004; 10 566
44. Coleman RS, Madaras ML. J. Org. Chem.: 1998; 63 5700
45. Coleman RS, Berg MA, Murphy CJ. Tetrahedron: 2007; 63 3450
46. Sarker SD, Waterman PG. J. Nat. Prod.: 1995; 58 1109
47. Horton DA, Bourne GT, Smythe ML. Chem. Rev.: 2003; 103 893
48. Borges F, Roleira F, Milhazes N, Santana L, Uriarte E. Curr. Med. Chem.: 2005; 12 887
49. Ngameni B, Touaibia M, Patnam R, Belkaid A, Sonna P, Ngadjui BT, Anabi B, Roy R. Phytochemistry: 2006; 67 2573
50. Su J, Wu Z.-J, Zhang W.-D, Zhang C, Li H.-L, Liu R.-H, Shen Y.-H. Chem. Pharm. Bull.: 2008; 56 589
51. Akak CM, Djama CM, Nkengfack AE, Tu P.-F, Lei L.-D. Fitoterapia: 2010; 81 873
52. Batsurén D, Batirov ÉKh, Malikov VM. Khim. Prir. Soedin.: 1982; 650; Chem. Nat. Compd. 1983, 18, 616
53. Vdovin AD, Batsurén D, Batirov ÉKh, Yagudaev MR, Malikov VM. Khim. Prir. Soedin.: 1983; 441; Chem. Nat. Compd. 1984, 19, 413
54. Aminov SD, Vakhabov AA. Dokl. Akad. Nauk SSSR: 1985; 44
55. O'Callaghan CN, Conalty ML. Proc. R. Ir. Acad., Sect. B: 1979; 6 87
56. Burke TR. Jr, Lim B, Marquez VE, Li Z.-H, Bolen JB, Stefanova I, Horak ID. J. Med. Chem.: 1993; 36 425
57. Toshima K, Matsuo G, Ishizuka T, Ushiki Y, Nakata M, Matsumura S. J. Org. Chem.: 1998; 63 2307
58. Telbani EE, Desoky SE, Hammad MA, Rahman AR. H. A, Schmidt RR. Eur. J. Org. Chem.: 1998; 2317
59. Oyama K, Kondo T. J. Org. Chem.: 2004; 69 5240
60. See also ref. 4k
61. Giguère D, Patnam R, Juarez-Ruiz JM, Neault M, Roy R. Tetrahedron Lett.: 2009; 50 4254
62. Giguère D, Cloutier P, Roy R. J. Org. Chem.: 2009; 74 8480
63. Bienaymé H, Hulme C, Oddon G, Schmitt P. Chem.-Eur. J.: 2000; 6 3321
64. Dömling A, Ugi I. Angew. Chem. Int. Ed.: 2000; 39 3168
65. Zhu J. Eur. J. Org. Chem.: 2003; 1133
66. Marcaccini S, Miguel D, Torroba T, García-Valverde M. J. Org. Chem.: 2003; 68 3315
67. Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L. Acc. Chem. Res.: 2003; 36 899
68. Appukkuttan P, Dehaen W, Fokin VV, Van der Eycken E. Org. Lett.: 2004; 6 4223
69. Byk G, Kabahn E. J. Comb. Chem.: 2004; 6 596
70. Liéby-Muller F, Constantieux T, Rodriguez J. J. Am. Chem. Soc.: 2005; 127 17176
71. Ramon DJ, Yus M. Angew. Chem. Int. Ed.: 2005; 44 1602
72. Multicomponent Reactions. Zhu J, Bienaymé H. Wiley-VCH Weinheim: 2005
73. Dömling A. Chem. Rev.: 2006; 106 17
74. Bae I, Han H, Chang S. J. Am. Chem. Soc.: 2005; 127 2038
75. Cho SH, Yoo EJ, Bae I, Chang S. J. Am. Chem. Soc.: 2005; 127 16046
76. Yoo EJ, Bae I, Cho SH, Han H, Chang S. Org. Lett.: 2006; 8 1347
77. Yoo EJ, Chang S. Curr. Org. Chem.: 2009; 13 1766
78. Lu P, Wang Y.-G. Synlett: 2010; 165
79. Kim SH, Park SH, Choi JH, Chang S. Chem.-Asian J.: 2011; 6 2618
80. Chang S, Lee M, Jung DY, Yoo EJ, Cho SH, Han SK. J. Am. Chem. Soc.: 2006; 128 12366
81. Yoo EJ, Ahlquist M, Kim SH, Bae I, Fokin VV, Sharpless KB, Chang S. Angew. Chem. Int. Ed.: 2007; 46 1730
82. Cho SH, Chang S. Angew. Chem. Int. Ed.: 2007; 46 1897
83. Cho SH, Chang S. Angew. Chem. Int. Ed.: 2008; 47 2836
84. Yoo EJ, Ahlquist M, Bae I, Sharpless KB, Fokin VV, Chang S. J. Org. Chem.: 2008; 73 5520
85. Kim J, Lee SY, Lee J, Do Y, Chang S. J. Org. Chem.: 2008; 73 9454
86. Yoo EJ, Chang S. Org. Lett.: 2008; 10 1163
87. Hwang SJ, Cho SH, Chang S. Pure Appl. Chem.: 2008; 80 873
88. Kim JY, Kim SH, Chang S. Tetrahedron Lett.: 2008; 49 1745
89. Yoo EJ, Park SH, Lee SH, Chang S. Org. Lett.: 2009; 11 1155
90. Lee MY, Kim MH, Kim J, Kim SH, Kim BT, Jeong IH, Chang S, Kim SH, Chang S.-Y. Bioorg. Med. Chem. Lett.: 2010; 20 541
91. Husmann R, Na YS, Bolm C, Chang S. Chem. Commun.: 2010; 46 5494
92. Cui S.-L, Lin X.-F, Wang Y.-G. Org. Lett.: 2006; 8 4517
93. Cui S.-L, Wang J, Wang Y.-G. Org. Lett.: 2007; 9 5023
94. Cui S.-L, Wang J, Wang Y.-G. Org. Lett.: 2008; 10 13
95. Cui S.-L, Wang J, Wang Y.-G. Org. Lett.: 2008; 10 1267
96. Cui S.-L, Wang J, Wang Y.-G. Tetrahedron: 2008; 64 487
97. Lu W, Song W, Hong D, Lu P, Wang Y.-G. Adv. Synth. Catal.: 2009; 351 1768
98. She J, Jiang Z, Wang Y.-G. Synlett: 2009; 2023
99. Jin H, Xu X, Gao J, Zhong J, Wang Y.-G. Adv. Synth. Catal.: 2010; 352 347
100. Shen Y, Cui S, Wang J, Chen X, Lu P, Wang Y.-G. Adv. Synth. Catal.: 2010; 352 1139
101. Song W, Lei M, Shen Y, Cai S, Lu W, Lu P, Wang Y.-G. Adv. Synth. Catal.: 2010; 352 2432
102. Song W, Lu W, Wang J, Lu P, Wang Y.-G. J. Org. Chem.: 2010; 75 3481
103. Wang J, Wang J, Zhu Y, Lu P, Wang Y.-G. Chem Commun.: 2011; 47 3275
104. Li Y, Hong D, Zhu Y, Lu P, Wang Y.-G. Tetrahedron: 2011; 67 8086
105. Cassidy MP, Raushel J, Fokin VV. Angew. Chem. Int. Ed.: 2006; 45 3154
106. Whiting M, Fokin VV. Angew. Chem. Int. Ed.: 2006; 45 3157
107. Mandal S, Gauniyal HM, Pramanik K, Mukhopadhyay B. J. Org. Chem.: 2007; 72 9753
108. Xu X, Cheng D, Li J, Guo H, Yan J. Org. Lett.: 2007; 9 1585
109. Wang F, Fu H, Jiang Y, Zhao Y. Adv. Synth. Catal.: 2008; 350 1830
110. Shang Y, He X, Hu J, Wu J, Zhang M, Yu S, Zhang Q. Adv. Synth. Catal.: 2009; 351 2709
111. Yao W, Pan L, Zhang Y, Wang G, Wang X, Ma C. Angew. Chem. Int. Ed.: 2010; 49 9210
112. Shang Y, Ju K, He X, Hu J, Yu S, Zhang M, Liao K, Wang L, Zhang P. J. Org. Chem.: 2010; 75 5743
113. Chen Z, Ye C, Gao L, Wu J. Chem. Commun.: 2011; 47 5623
114. Chen Z, Zheng D, Wu J. Org. Lett.: 2011; 13 848
115. Li S, Luo Y, Wu J. Org. Lett.: 2011; 13 3190
116. Li S, Luo Y, Wu J. Org. Lett.: 2011; 13 4312
117. Namitharan K, Pitchumani K. Org. Lett.: 2011; 13 5728
118. Liu Y, Wang X, Xu J, Zhang Q, Zhao Y, Hu Y. Tetrahedron: 2011; 67 6294
119. Kaliappan KP, Subrahmanyam AV. Org. Lett.: 2007; 9 1121
120. Kaliappan KP, Kalanidhi P, Mahapatra S. Synlett: 2009; 2162
121. Subrahmanyam AV, Palanichamy K, Kaliappan KP. Chem.-Eur. J.: 2010; 16 8545
122. Khangarot RK, Kaliappan KP. Eur. J. Org. Chem.: 2011; 6117
123. Betkekar VV, Panda S, Kaliappan KP. Org. Lett.: 2012; 14 198
124. Alkyne 10 was synthesized by methylation of the corresponding propargylic tertiary alcohol, see: Ramana CV, Mallik R, Gonnade RG. Tetrahedron: 2008; 64 219