Transition-Metal-Free Arylation of N -Alkyl-tetrahydroisoquinolines under Oxidative Conditions: A Convenient Synthesis of C1-Arylated Tetrahydro-isoquinoline Alkaloids

Synthesis (Germany)

Volumn 46, Issue 19, 2014, Pages 2644-2650

  Singh, Kamal Nain ^a   Kessar, Satinder V ^a   Singh, Paramjit ^a   Singh, Pushpinder ^b   Kaur, Manjot ^a   Batra, Aanchal ^a  

^a PANJAB UNIVERSITY   (India)

^b DAV University   (India)

Author keywords

alkaloids; arylation; C H activation; metal free; tetrahydroisoquinoline

Indexed keywords

ACTIVATION ANALYSIS; ALKALOIDS; CHEMICAL ACTIVATION; CHEMICAL REACTIONS; METABOLITES; TRANSITION METALS;

ARYLATIONS; C-H ACTIVATION; DIETHYL AZODICARBOXYLATE; METAL FREE; METAL-FREE CONDITIONS; NATURALLY OCCURRING; OXIDATIVE CONDITIONS; TETRAHYDROISOQUINOLINES;

AROMATIC COMPOUNDS;

1 (2 METHOXYNAPHTHALEN 1 YL) 2 METHYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 1 (3,4 DIMETHOXYPHENYL) 2 METHYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 1 (3,4 DIMETHOXYPHENYL) 6,7 DIMETHOXY 2 METHYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 1 (4 METHOXYPHENYL) 2 METHYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 BENZYL 1 (4 METHOXYPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 BENZYL 1 PHENYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 ETHYL 6,7 DIMETHOXY 1 (4 METHOXYPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 ETHYL 6,7 DIMETHOXY 1 PHENYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 METHYL 1 (NAPHTHALEN 1 YL) 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 METHYL 1 (PARA TOLYL) 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 METHYL 1 PHENYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 6,7 DIMETHOXY (3 METHOXYPHENYL) 2 METHYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 6,7 DIMETHOXY 1 (4 METHOXYPHENYL) N METHYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 6,7 DIMETHOXY 2 METHYL 1 (3,4,5 TRIMETHOXYPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE; 6,7 DIMETHOXY 2 METHYL 1 (NAPHTHALEN 1 YL) 1,2,3,4 TETRAHYDROISOQUINOLINE; 6,7 DIMETHOXY 2 METHYL 1 (PARA TOLYL) 1,2,3,4 TETRAHYDROISOQUINOLINE; 6,7 DIMETHOXY 2 METHYL 1 PHENYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 7 ETHOXY 6 METHOXY 1 (4 METHOXYPHENYL) 2 METHYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 7 ETHOXY 6 METHOXY 2 METHYL 1 PHENYL 1,2,3,4 TETRAHYDROISOQUINOLINE; ALKALOID DERIVATIVE; CARBOXYLIC ACID; DIETHYL AZODICARBOXYLIC ACID; N ALKYL TETRAHYDROISOQUINOLINE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; PROCESS DEVELOPMENT;

EID: 84920092715     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0034-1378337     Document Type: Article

References (97)

1. Wang S., Onaran M. B., Seto C. T. Org. Lett.: 2010; 12 2690
2. Bentley K. W. Nat. Prod. Rep.: 2005; 22 249
3. Scott J. D., Williams R. M. Chem. Rev.: 2002; 102 1669
4. Ozturk T. The Alkaloids. Vol. 53 Cordell G. A. Academic Press New York: 2000; 120
5. Charifson P. S. Drugs Future: 1989; 14 1179
6. Menarchery M. D., Lavanier G. L., Wetherly M. L., Guinaudeau H., Shamma M. J. Nat. Prod.: 1986; 49 745
7. Wu W., Beal J. L., Fairchild E. H., Doskotch R. W. J. Org. Chem.: 1978; 43 580
8. Chen K.-X, Xie H.-Y, Li Z.-G. Bioorg. Med. Chem. Lett.: 2008; 18 5381
9. Cheng P., Huang N., Zhang Q., Zheng Y.-T. Bioorg. Med. Chem. Lett.: 2008; 18 2475
10. Kuo C.-Y, Wu M. J., Kuo Y.-H. Eur. J. Med. Chem.: 2006; 41 940
11. Kim S. A., Kwon Y., Kim J. H., Muller M. T., Chung I. K. Biochemistry: 1998; 37 16316
12. Tiwari R. K., Singh D., Singh J., Chhiller A. K. Eur. J. Med. Chem.: 2006; 41 40
13. Minor D. L., Wyrick S. D., Charifson P. S., Watts V. J., Nichols D. E., Mailman R. B. J. Med. Chem.: 1994; 37 4317
14. Charifson P. S., Wyrick S. D., Ademe Simmons R. M., McDougald D. L., Mailman R. B., Hoffman A. J., Bowen J. P. J. Med. Chem.: 1988; 31 1941
15. Gao M., Kong D., Clearfield A., Zheng Q.-H. Bioorg. Med. Chem. Lett.: 2006; 16 2229
16. Ludwig M., Hoesl C. E., HÖfner G., Wanner K. T. Eur. J. Med. Chem.: 2006; 41 1003
17. Naito R., Yonetoku Y., Okamoto Y., Toyoshima A., Ikeda K., Takeuchi M. J. Med. Chem.: 2005; 48 6597
18. Ohtake A., Ukai M., Hatanaka T., Kobayashi S., Ikeda K., Sato S., Miyata K., Sasamata M. Eur. J. Pharmacol.: 2004; 492 243
19. Kurihara K., Yamamoto Y., Miyaura N. Adv. Synth. Catal.: 2009; 351 260
20. Seayad J., Seayad A. M., List B. J. Am. Chem. Soc.: 2006; 128 1086
21. Taylor M. S., Jacobsen E. N. J. Am. Chem. Soc.: 2004; 126 10558
22. Gitto R., Barreca M. L., Luca L. D., Sarro G. D., Ferrerri G. J. Med. Chem.: 2003; 46 197
23. Ruchirawat S., Bhavakul V., Chaisupakitsin M. Synth. Commun.: 2003; 33 621
24. Yamada H., Kawate T., Matsumizu M., Nishida A., Yamaguchi K., Nakagawa M. J. Org. Chem.: 1998; 63 6348
25. Cox E. D., Cook J. M. Chem. Rev.: 1995; 95 1797
26. Berenguer I., Aouad N. E., Andujar S., Romero V., Suvire F., Freret T. Bioorg. Med. Chem.: 2009; 17 4968
27. Doi S., Shirai N., Sato Y. J. Chem. Soc., Perkin Trans. 1: 1997; 2217
28. Suzuki H., Aoyagi S., Kibayashi C. Tetrahedron Lett.: 1995; 36 6709
29. Landais Y., Robin J.-P. Tetrahedron: 1992; 48 7185
30. Gray N. M., Cheng B. K., Mick S. J., Lair C. M., Contreras P. C. J. Med. Chem.: 1989; 32 1242
31. Leander K., Luning B. Tetrahedron Lett.: 1968; 9 1393
32. Ishiwata S., Itakura K. Chem. Pharm. Bull.: 1968; 16 778
33. Reeve W., Eareckson W. M. J. Am. Chem. Soc.: 1950; 72 5195
34. Abe K., Saitoh T., Horiguchi Y., Utsunomiya I., Taguchi K. Biol. Pharm. Bull.: 2005; 28 1355
35. Bender C., Liebscher J. ARKIVOC: 2009; (vi) 111
36. Costa B. R., Radesca L. Synthesis: 1992; 887
37. Takano S., Suzuki M., Kijima A., Ogasawara K. Chem. Lett.: 1990; 315
38. Nobuta T., Fujiya A., Yamaguchi T., Tada N., Miura T., Itoh A. RSC Adv.: 2013; 3 10189
39. Hari D. P., Konig B. Org. Lett.: 2011; 13 3852; and references therein
40. Murahashi S.-I, Nakae T., Terai H., Komiya N. J. Am. Chem. Soc.: 2008; 130 11005
41. Li Z., Yu R., Li H. Angew. Chem. Int. Ed.: 2008; 47 7497
42. Li Z., MacLeod P. D., Li C.-J. Tetrahedron: Asymmetry: 2006; 17 590
43. Li Z., Li C.-J. J. Am. Chem. Soc.: 2005; 127 3672
44. Li Z., Li C.-J. Eur. J. Org. Chem.: 2005; 3173
45. Li Z., Li C.-J. J. Am. Chem. Soc.: 2004; 126 11810
46. Park S. J., Price J. R., Todd M. H. J. Org. Chem.: 2012; 77 949
47. Dhineshkumar J., Lamani M., Alagiri K., Prabhu K. R. Org. Lett.: 2013; 15 1092
48. Alagiri K., Devadig P., Prabhu K. R. Chem. Eur. J.: 2012; 18 5160
49. Ghobrial M., Schnürch M., Mihovilovic M. D. J. Org. Chem.: 2011; 76 8781
50. Tsang A. S.-K, Todd M. H. Tetrahedron Lett.: 2009; 50 1199
51. Zhong J.-J, Meng Q.-Y, Wang G.-X, Chen B., Feng K., Tung C.-H, Wu L.-Z. Chem. Eur. J.: 2013; 19 6443
52. Boess E., Schmitz C., Klussmann M. J. Am. Chem. Soc.: 2012; 134 5317
53. Ghobrial M., Harhammer K., Mihovilovic M. D., Schnürch M. Chem. Commun.: 2010; 46 8836
54. Li Z., Li C.-J. J. Am. Chem. Soc.: 2005; 127 6968
55. Li Z., Bohle D. S., Li C.-J. Proc. Natl. Acad. Sci. U.S.A.: 2006; 103 8928
56. Baslé O., Li C.-J. Org. Lett.: 2008; 10 3661
57. Tsang A. S.-K, Ingram K., Keiser J., Hibbert D. B., Todd M. H. Org. Biomol. Chem.: 2013; 11 4921
58. Schweitzer-Chaput B., Klussmann M. Eur. J. Org. Chem.: 2013; 666
59. Xie Z., Liu L., Chen W., Zheng H., Hu Q., Yuan H., Lou H. Angew. Chem. Int. Ed.: 2014; 53 3904
60. Muramatsu W., Nakano K., Li C.-J. Org. Lett.: 2013; 15 3650
61. Muramatsu W., Nakano K., Li C.-J. Org. Biomol. Chem.: 2014; 12 2189
62. Chen W., Zheng H., Pan X., Xie Z., Zan X., Sun B., Liu L., Lou H. Tetrahedron Lett.: 2014; 55 2879
63. Chu L., Zhang X., Qing F.-L. Org. Lett.: 2009; 11 2197
64. Son Y. W., Kwan T. H., Lee J. K., Pae A. N., Lee J. Y., Cho Y. S., Min S.-J. Org. Lett.: 2011; 13 6500
65. Schrittwieser J. H., Resch V., Sattler J. H., Lienhart W.-D, Durchschein K., Winkler A., Gruber K., Macheroux P., Kroutil W. Angew. Chem. Int. Ed.: 2011; 50 1068
66. Allen J. M., Lambert T. H. J. Am. Chem. Soc.: 2011; 133 1260
67. Deb M. L., Dey S. S., Bento I., Barros M. T., Maycock C. D. Angew. Chem. Int. Ed.: 2013; 52 9791
68. Kessar S. V., Singh P., Vohra R., Kaur N. P., Singh K. N. J. Chem. Soc., Chem. Commun.: 1991; 568
69. Kessar S. V., Singh P. Chem. Rev.: 1997; 97 721
70. Singh K. N., Singh P., Singh P., Deol Y. S. Org. Lett.: 2012; 14 2202
71. Singh K. N., Singh P., Sharma E., Deol Y. S. Synthesis: 2014; 46 1739
72. Singh K. N., Singh P., Singh P., Maheshwary Y., Kessar S. V., Batra A. Synlett: 2013; 24 1963
73. Singh P., Batra A., Singh P., Kaur A., Singh K. N. Eur. J. Org. Chem.: 2013; 7688
74. Singh K. N., Singh P., Kaur A., Singh P. Synlett: 2012; 23 760
75. Xu X., Li X. Org. Lett.: 2009; 11 1027
76. Su W., Yu J., Li Z., Jiang Z. J. Org. Chem.: 2011; 76 9144
77. Cosner C. C., Cabrera P. J., Byrd K. M., Thomas A. M. A, Helquist P. Org. Lett.: 2011; 13 2071
78. Damu G. L. V, Selvam J. P., Rao C. V., Venkateswarlu Y. Tetrahedron Lett.: 2009; 50 6154
79. Zhang Y., Li C.-J. J. Am. Chem. Soc.: 2006; 128 4242
80. Walker D., Hiebert J. D. Chem. Rev.: 1967; 67 153
81. Fu P. P., Harvey R. G. Chem. Rev.: 1978; 78 317
82. Zhang J., Zhu D., Yu C., Wan C., Wang Z. Org. Lett.: 2010; 12 2841
83. We are grateful to the reviewers for bringing to our notice in reference 9b the references numbered 15, 17 and 24 which are related to our work.
84. Xu X., Li X., Ma L., Ye N. J. Am. Chem. Soc.: 2008; 130 14048
85. Wilson M. W., Govindachari T. R. Org. React.: 1951; 6 74
86. Marsden R., MacLean D. B. Can. J. Chem.: 1984; 62 1392
87. Miller R. B., Tsang T. Tetrahedron Lett.: 1988; 29 6715
88. Kajita M., Niwa T., Fujisaki M., Ueki M., Niimura K. J. Chromatogr. B: 1995; 669 345
89. Li C.-J, Mcleod P., Li Z. P., Feng J. WO 2007,098,608: 2007
90. Valpuesta M., Ariza M., Diaz A., Suau R. Eur. J. Org. Chem.: 2010; 4393
91. Jiashou W., Jian L., Jin Z., Jingen D. Synlett: 2006; 2059
92. Ahluwalia G. S., Narang K. S., Rây J. N. J. Chem. Soc.: 1931; 2057
93. Ariza M., Diaz A., Suau R., Valpuesta M. Eur. J. Org. Chem.: 2011; 6507
94. Voskressensky L. G., Listratova A. V., Borisova T. N., Alexandrov G. G., Varlamov A. V. Eur. J. Org. Chem.: 2007; 6106
95. Ye Z.-S, Guo R.-N, Cai X.-F, Chen M.-W, Shi L., Zhou Y.-G. Angew. Chem. Int. Ed.: 2013; 52 3685
96. Umetsu K., Asao N. Tetrahedron Lett.: 2008; 49 2722
97. Samano V., Ray J. A., Thompson J. B., Mook R. A., Jung D. K., Koble C. S., Martin M. T., Bigham E. C., Regitz C. S., Feldman P. L. Org. Lett.: 1999; 1 1993