Microwave-assisted synthesis of pyrazino[2,1-b]quinazolines and 3-indolyl-2(1H)-pyrazinones employing a chemoselective silver(I)- and gold(I)-catalyzed reaction

Advanced Synthesis and Catalysis

Volumn 354, Issue 8, 2012, Pages 1593-1599

  Vachhani, Dipak D ^a   Mehta, Vaibhav P ^a   Modha, Sachin G ^a,b   Van Hecke, Kristof ^a,c   Vanmeervelt, Luc ^a   Van Der Eycken, Erik V ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b C 5 Rushikesh Apartment ^*  (India)

^c GHENT UNIVERSITY   (Belgium)

Author keywords

gold; heteroannulation; homogenous catalysis; hydroamination; microwave irradiation; pyrazinones; silver

Indexed keywords

EID: 84861541984     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100881     Document Type: Article

References (108)

1. N. Chernyak, V. Gevorgyan, Angew. Chem. 2010, 122, 2803
2. Angew. Chem. Int. Ed. 2010, 49, 2743
3. K. E. Lazarski, D. X. Hu, C. L. Stern, R. J. Thomson, Org. Lett. 2010, 12, 3010
4. C. J. Tan, Y. T. Di, Y. H. Wang, Y. Zhang, Y. K. Si, Q. Zhang, S. Gao, X. J. Hu, X. Fang, S. F. Li, X. J. Hao, Org. Lett. 2010, 12, 2370
5. Y. Murata, D. Yamashita, K. Kitahara, Y. Minasako, A. Nakazaki, S. Kobayashi, Angew. Chem. 2009, 121, 1428
6. Angew. Chem. Int. Ed. 2009, 48, 1400
7. D. Yang, G. C. Micalizio, J. Am. Chem. Soc. 2009, 131, 17548.
8. Metal Catalyzed Coupling Reactions, 2 nd edn., (Eds.:, A. de Meijere, F Diederich,), Wiley-VCH, Weinheim, 2004
9. E-i. Negishi, Acc. Chem. Res. 1982, 15, 340-348
10. P. Knochel, M. I. Calaza, E. Hupe, in: Metal catalysed Cross-Coulping Reactions, Vol. 1, Chapter 11, Wiley-VCH: Weinheim, Germany, 2004
11. Transition Metals for Organic Synthesis, (Eds.:, M. Beller, C. Bolm,), 2 nd edn., Wiley-VCH, Weinheim, 2004
12. E. A. V. Kentchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824
13. Angew. Chem. Int. Ed. 2007, 46, 2768. For a pertinent review on hydroamination, see
14. T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795. For alkyne hydroamination to give indoles, see
15. A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610
16. M. Alfonsi, A. Arcadi, M. Aschi, G. Bianchi, F. Marinelli, J. Org. Chem. 2005, 70, 2265
17. Y. Miyazaki, S. Kobayashi, J. Combi. Chem. 2008, 10, 355. For Ir-catalyzed reactions see
18. X. Li, A-R Chianese, T. Vogel, R. H. Crabtree, Org. Lett. 2005, 7, 5437; For the Pt(IV)-catalyzed reaction, see
19. N. T. Patil, R. D. Kavthe, V. D. Shinde, B. Sridhar, J. Org. Chem. 2010, 75, 3371.
20. For a thematic special issue on coinage metals in organic synthesis, see: Chem. Rev. 2008, 108, Issue 8.
21. M. Sawamura, Y. Ito, Chem. Rev. 1992, 92, 857. For selected recent reviews on gold catalysis, see
22. G. Dyker, Angew. Chem. 2000, 112, 4407
23. Angew. Chem. Int. Ed. 2000, 39, 4237
24. A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064
25. Angew. Chem. Int. Ed. 2006, 45, 7896
26. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180
27. A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478
28. Angew. Chem. Int. Ed. 2007, 46, 3410
29. D. J. Gorin, F. D. Toste, Nature 2007, 446, 395
30. A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37, 1766
31. J. Muzart, Tetrahedron 2008, 64, 5815
32. Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239
33. A. Arcadi, Chem. Rev. 2008, 108, 3266
34. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351
35. R. Skouta, C.-J Li, Tetrahedron 2008, 64, 4917
36. R. A. Widenhoefer, Chem. Eur. J. 2008, 14, 5382
37. N. Bongers, N. Krause, Angew. Chem. 2008, 120, 2208
38. Angew. Chem. Int. Ed. 2008, 47, 2178
39. N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395
40. D. J. Gorin, F. D. Toste, Chem. Rev. 2008, 108, 3395
41. S. F. Krisch, Synthesis 2008, 3183
42. A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208
43. P. Belmont, E. Parker, Eur. J. Org. Chem. 2009, 6075
44. N. Shapiro, F. D. Toste, Synlett 2010, 675
45. S. Sengupta, X. Shi, ChemCatChem 2010, 2, 609
46. A. S. K. Hashmi, Angew. Chem. 2010, 122, 5360
47. Angew. Chem. Int. Ed. 2010, 49, 5232
48. A. S. K. Hashmi, M. Bührle, Aldrichimica Acta 2010, 43, 27
49. A. S. Dudnik, N. Chernyak, V. Gevorgyan, Aldrichimica Acta 2010, 43, 37
50. N. Krause, C. Winter, Chem. Rev. 2011, 111, 1994
51. M. Rudolph, A. S. K. Hashmi, Chem. Commun. 2011, 47, 6536. For a recent review on gold-catalyzed oxidative-couplings, see
52. M. N. Hopkinson, A. D. Gee, V. Gouverneur, Chem. Eur. J. 2011, 17, 8248; for a pertinent review on gold-catalyzed C-H activation and functionalization, see
53. T. C. Boorman, I. Larrosa, Chem. Soc. Rev. 2011, 40, 1910
54. T. de Haro, C. Nevado, Synthesis 2011, 2530; for an excellent recent review on gold oxo-carbenoids, see
55. J. Xiao, X. Li, Angew. Chem. 2011, 123, 7364
56. Angew. Chem. Int. Ed. 2011, 50, 7226.
57. U. Halbes-Letinos, J.-M. Weibel, P. Pale, Chem. Soc. Rev. 2007, 36, 759
58. J.- M. Weibel, A. Blanc, P. Pale, Chem. Rev. 2008, 108, 3149
59. M. Alvarez-Corral, M. Munoz-Dorado, I. Rodriguez-Garcia, Chem. Rev. 2008, 108, 3174
60. M. Naodovic, H. Yamamoto, Chem. Rev. 2008, 108, 3132
61. Silver in Organic Chemistry, (Ed.:, M. Harmata,), John Wiley & Sons, Hoboken, 2010. For selected examples, see
62. S. Agarwal, S.; H.-J. Knolker, Org. Biomol. Chem. 2004, 2, 3060
63. Q. Huang, J. A. Hunter, R. C. Larock, Org. Lett. 2001, 3, 2973
64. N. Asao, S. Yudha, T. Nogami, Y. Yamamoto, Angew. Chem. 2005, 117, 5662
65. Angew. Chem. Int. Ed. 2005, 44, 5526
66. S. Su, J. A. Porco, Jr. , J. Am. Chem. Soc. 2007, 129, 7744
67. N. Ghavtadze, R. Frohlich, E.-U. Würthwein, Eur. J. Org. Chem. 2010, 1787
68. Z. Chen, X. Yu, J Wu, Chem. Commun. 2010, 46, 6356. For a selected contribution from our laboratory, see
69. D. S. Ermolat'ev, V. P. Mehta, E. V. Van der Eycken, Synlett 2007, 3117
70. V. P. Mehta, S. G. Modha, D. S. Ermolat'ev, K. Van Hecke, L. Van Meervelt, E. V. Van der Eycken, Aust. J. Chem. 2009, 62, 27
71. D. S. Ermolat'ev, J. B. Bariwal, H. P. L. Steenackers, S. C. J. De Keersmaecker, E. V. Van der Eycken, Angew. Chem. 2010, 122, 9655
72. Angew. Chem. Int. Ed. 2010, 49, 9465
73. O. P. Pereshivko, V. A. Peshkov, D. S. Ermolat'ev, S. Van Hove, K. Van Hecke, L. Van Meervelt, E. V. Van der Eycken, Synthesis 2011, 1587
74. V. A. Peshkov, O. P. Pereshivko, S. Sharma, T. Meganathan, V. S. Parmar, D. S. Ermolat'ev, E. V. Van der Eycken, J. Org. Chem. 2011, 76, 5867.
75. I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127
76. G. Zeni, R. C. Larock, Chem. Rev. 2004, 104, 2285
77. F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079
78. S. A. Vizer, K. B. Yerzhanov, A. Al Aziz Al Quntar, V. M. Dembitsky, Tetrahedron 2004, 60, 5499
79. B. Godoi, R. F. Schumacher, G. Zeni, Chem. Rev. 2011, 111, 2937. For the synthesis of heterocycles via Pd-catalyzed oxidative additions, see
80. G. Zeni, R. C. Larock, Chem. Rev. 2006, 106, 4644.
81. G. Hoornaert, Bull. Soc. Chim. Belg. 1994, 103, 583. For recent reviews see
82. V. G. Pawar, W. M. De Borggraeve, Synthesis 2006, 2799; using microwave irradiation, see
83. V. P. Mehta, P. Appukkuttan, E. Van der Eycken, Curr. Org. Chem. 2011, 15, 265
84. Topics in Heterocyclic Chemistry, Vol. 1, (Eds.:, E. Van der Eycken, C. O. Kappe,), Springer, Berlin, 2006, p 267
85. N. Kaval, K. Bisztray, W. Dehaen, C. O. Kappe, E. Van der Eycken, Mol. Diversity 2003, 7, 125
86. N. Kaval, B. K. Singh, D. S. Ermolat'ev, S. Claerhout, J. Van der Eycken, E. Van der Eycken, J. Comb. Chem. 2007, 9, 446.
87. V. P. Mehta, A. Sharma, E. Van der Eycken, Adv. Synth. Catal. 2008, 350, 2174
88. V. P. Mehta, A. Sharma, E. Van der Eycken, Org. Lett. 2008, 10, 1147
89. V. P. Mehta, S. G. Modha, E. Van der Eycken, J. Org. Chem. 2009, 74, 6870.
90. M. D. Burke, E. M. Berger, S. L. Schreiber, Science 2003, 302, 613
91. D. R. Spring, Org. Biomol. Chem. 2003, 1, 3867
92. M. D. Burke, G. Lalic, Chem. Biol. 2002, 9, 535
93. S. L. Schreiber, Science 2000, 287, 1964.
94. J. Vekemans, C. Pollers-Wieërs, G. Hoornaert, J. Heterocycl. Chem. 1983, 20, 919. For a recent microwave-assisted synthesis, see
95. J. Gising, P. Örtqvist, A. Sandström, M. Larhed, Org. Biomol. Chem. 2009, 7, 2809.
96. A. Tahri, W. De Borggraeve, K. Buysens, L. Van Meervelt, F. Compernolle, G. J. Hoornaert, Tetrahedron 1999, 55, 14675.
97. R. K. Prajapati, J. Kumar, S. Verma, Chem. Commun. 2010, 46, 3312
98. N. T. Patil, V. Singh, J. Organomet. Chem. 2011, 696, 419.
99. C. Ferrer, A. M. Echavarren, Angew. Chem. 2006, 118, 1123
100. Angew. Chem. Int. Ed. 2006, 45, 1105
101. J-E. Kano, H-B. Kim, J-W. Lee, S. Shin, Org. Lett. 2006, 8, 3537
102. C. Ferrer, C. H. M. Amijs, A. M. Echavarren, Chem. Eur. J. 2007, 13, 1358
103. R. Sanz, D. Miguel, F. Rodriguez, Angew. Chem. 2008, 120, 7464
104. Angew. Chem. Int. Ed. 2008, 47, 7354
105. Y. Lu, X. Du, X. Jia, Y. Liu, Adv. Synth. Catal. 2009, 351, 1517
106. G. Li, Y. Liu, J. Org. Chem. 2010, 75, 3526
107. N. R. Pearl, N. D. Ide, S. Prajapati, H. H. Perfect, S. G. Duron, D. Y. Gin, J. Am. Chem. Soc. 2010, 132, 1802
108. K. Hirano, Y. Inaba, T. Watanabe, S. Oishi, N. Fujii, H. Ohno, Adv. Synth. Catal. 2010, 352, 368.