An oxidant-free single-step synthesis of tetra-or disubstituted symmetrical pyridine derivatives by a Hf(OTf)4-catalyzed annulation

Synlett

Volumn , Issue 14, 2011, Pages 2029-2034

  Sasada, Toshiaki ^a   Kobayashi, Fuminori ^a   Moriuchi, Masato ^a   Sakai, Norio ^a   Konakahara, Takeo ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

enamines; hafnium triflate; heterocycles; orthoesters; pyridines

Indexed keywords

ACETOPHENONE DERIVATIVE; AMMONIUM ACETATE; PYRIDINE DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STOICHIOMETRY; SYNTHESIS;

EID: 80052064489     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1260978     Document Type: Article

References (149)

1. Henry G D., Tetrahedron 2004 60 6043
2. For selected recent books and reviews, see: Name Reactions in Heterocyclic Chemistry Li J J. John Wiley Hoboken 2005 301-374
3. Candeias N R., Branco L C., Gois P M. P., Afonso C A. M., Trindade A F., Chem. Rev. 2009 109 2703
4. Hemming K, Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 2009 105 129
5. Varela J A., Saa C, Synlett 2008 2571
6. Donohoe T J., Fishlock L P., Procopiou P A., Chem. Eur. J. 2008 14 5716
7. Bagley M C., Glover C, Merritt E A., Synlett 2007 2459
8. DSouza D M., Müller T J. J., Chem. Soc. Rev. 2007 36 1095
9. Heller B, Hapke M, Chem. Soc. Rev. 2007 36 1085
10. Mangelinckx S, Giubellina N, DeKimpe N, Chem. Rev. 2004 104 2353
11. Varela J A., Saa C, Chem. Rev. 2003 103 3787
12. For selected recent papers on the multicomponent synthesis of pyridines, see:, Lechel T, Dash J, Hommes P, Lentz D, Reissig H.-U, J. Org. Chem. 2010 75 726
13. Sha F, Huang X, Angew. Chem. Int. Ed. 2009 48 3458
14. Kobayashi T, Hatano S, Tsuchikawa H, Katsumura S, Tetrahedron Lett. 2008 49 4349
15. Dash J, Lechel T, Reissig H.-U, Org. Lett. 2007 9 5541
16. Schramm O G., Dediu N, Oeser T, Müller T J. J., J. Org. Chem. 2006 71 3494
17. Senaiar R S., Young D D., Deiters A, Chem. Commun. 2006 1313
18. Tanaka R, Yuza A, Watai Y, Suzuki D, Takayama Y, Sato F, Urabe H, J. Am. Chem. Soc. 2005 127 7774
19. Suzuki D, Nobe Y, Watai Y, Tanaka R, Takayama Y, Sato F, Urabe H, J. Am. Chem. Soc. 2005 127 7474
20. Dediu O G., Yehia N A. M., Oeser T, Polborn K, Müller T J. J., Eur. J. Org. Chem. 2005 1834
21. For selected recent papers on the metal-mediated synthesis of pyridines, see:, Wang Y.-F, Chiba S, J. Am. Chem. Soc. 2009 131 12570
22. Yoshida K, Kawagoe F, Hayashi K, Horiuchi S, Imamoto T, Yanagisawa A, Org. Lett. 2009 11 515
23. Chiba S, Xu Y.-J, Wang Y.-F, J. Am. Chem. Soc. 2009 131 12886
24. Manning J R., Davies H M. L., J. Am. Chem. Soc. 2008 130 8602
25. Parthasarathy K, Jeganmohan M, Cheng C.-H, Org. Lett. 2008 10 325
26. Colby D A., Bergman R G., Ellman J A., J. Am. Chem. Soc. 2008 130 3645
27. Donohoe T J., Fishlock L P., Procopiou P A., Org. Lett. 2008 10 285
28. Yu N, Wang C, Zhao F, Liu L, Zhang W.-X, Xi Z, Chem. Eur. J. 2008 14 5670
29. Trost B M., Gutierrez A C., Org. Lett. 2007 9 1473
30. Tanaka K, Hara H, Nishida G, Hirano M, Org. Lett. 2007 9 1907
31. Chang H.-T, Jeganmohan M, Cheng C.-H, Org. Lett. 2007 9 505
32. Movassaghi M, Hill M D., J. Am. Chem. Soc. 2006 128 4592
33. Tekavec T N., Zuo G, Simon K, Louie J, J. Org. Chem. 2006 71 5834
34. Wang C, Wang Z, Liu L, Wang C, Liu G, Xi Z, J. Org. Chem. 2006 71 8565
35. Yamamoto Y, Kinpara K, Saigoku T, Takagishi H, Okuda S, Nishiyama H, Itoh K, J. Am. Chem. Soc. 2005 127 605
36. Varela J A., Castedo L, Saa C, J. Org. Chem. 2003 68 8595
37. Abbiati G, Arcadi A, Bianchi G, DiGiuseppe S, Marinelli F, Rossi E, J. Org. Chem. 2003 68 6959
38. Aelterman W, deKimpe N, Tyvorskii V, Kulinkovich O, J. Org. Chem. 2001 66 53
39. For selected recent papers on the synthesis of pyridines via the Hetero-Diels-Alder reaction, see:, Barluenga J, Fernandez-Rodriguez M A., Garcia-Garcia P, Aguilar E, J. Am. Chem. Soc. 2008 130 2764
40. Delaney P M., Huang J, Macdonald S J. F., Harrity J P. A., Org. Lett. 2008 10 781
41. Lu J.-Y, Arndt H.-D, J. Org. Chem. 2007 72 4205
42. Palacios F, Herran E, Alonso C, Rubiales G, Lecea B, Ayerbe M, Cossio F P., J. Org. Chem. 2006 71 6020
43. Sainz Y F., Raw S A., Taylor R J. K., J. Org. Chem. 2005 70 10086
44. Palacios F, Alonso C, Rubiales G, Villegas M, Tetrahedron 2005 61 2779
45. Palacios F, Alonso C, Amezua P, Rubiales G, J. Org. Chem. 2002 67 1941
46. For selected recent papers on the single-step Hantzsch-type synthesis of pyridines, see:, Sridhar M, Ramanaiah B C., Narsaiah C, Mahesh B, Kumaraswamy M, Mallu K K. R., Ankathi V M., Rao P S., Tetrahedron Lett. 2009 50 3897
47. Zhou Y, Sato Y, Kijima T, Izumi T, Synlett 2008 1999
48. Yadav A K., Yadav S K. S., Siddiqui I, Peruncheralathan S, Ila H, Junjappa H, Synlett 2008 2674
49. Lieby-Muller F, Allais C, Constantieux T, Rodriguez J, Chem. Commun. 2008 4207
50. Kim S H., Kim K H., Kim H S., Kim J N., Tetrahedron Lett. 2008 49 1948
51. Hu J, Zhang Q, Yuan H, Liu Q, J. Org. Chem. 2008 73 2442
52. Craig D, Paina F, Smith S C., Chem. Commun. 2008 3408
53. Borthakur M, Dutta M, Gogoi S, Boruah R C., Synlett 2008 3125
54. Ranu B C., Jana R, Sowmiah S, J. Org. Chem. 2007 72 3152
55. Evdokimov N M., Kireev A S., Yakovenko A A., Antipin M Y., Magedov I V., Kornienko A, J. Org. Chem. 2007 72 3443
56. Guo K, Thompson M J., Reddy T R. K., Mutter R, Chen B, Tetrahedron 2007 63 5300
57. Bagley M C., Chapaneri K, Dale J W., Xiong X, Bower J, J. Org. Chem. 2005 70 1389
58. Bagley M C., Dale J W., Bower J, Chem. Commun. 2002 1682
59. For selected recent papers on the single-step Hantzsch-type synthesis of symmetrical pyridines, see:, Zhu S.-L, Ji S.-J, Su X.-M, Sun C, Liu Y, Tetrahedron Lett. 2008 49 1777
60. DePaolis O, Baffoe J, Landge S M., Torok B, Synthesis 2008 3423
61. For selected recent reviews on the synthesis and aromatization of 1,4-dihydropyridines, see:, Saini A, Kumar S, Sandhu J S., J. Sci. Ind. Res. 2008 67 95
62. Quirion J C., Leclerc E, Jubault P, Sci. Synth. 2007 33 601
63. Simon C, Constantieux T, Rodriguez J, Eur. J. Org. Chem. 2004 4957
64. VandenEynde J J., Mayence A, Molecules 2003 8 381
65. Horton D A., Bourne G T., Smythe M L., Chem. Rev. 2003 103 893
66. For selected recent papers on the synthesis of 1,4-dihydropyridines, see:, Baskovc J, Bevk D, Stanovnik B, Svete J, J. Comb. Chem. 2009 11 500
67. D R B., Massi A, Noseda M D., Duarte M E. R., Dondoni A, Org. Biomol. Chem. 2009 7 1980
68. Kumar A, Maurya R A., Synlett 2008 883
69. Debache A, Boulcina R, Belfaitah A, Rhouati S, Carboni B, Synlett 2008 509
70. Bridgwood K L., Veitch G E., Ley S V., Org. Lett. 2008 10 3627
71. Palacios F, Herran E, Rubiales G, Alonso C, Tetrahedron 2007 63 5669
72. Bisht S S., Dwivedi N, Tripathi R P., Tetrahedron Lett. 2007 48 1187
73. Evdokimov N M., Magedov I V., Kireev A S., Kornienko A, Org. Lett. 2006 8 899
74. Wang G.-W, Xia J.-J, Miao C.-B, Wu X.-L, Bull. Chem. Soc. Jpn. 2006 79 454
75. Sridhar R, Perumal P T., Tetrahedron 2005 61 2465
76. Legeay J.-C, VandenEynde J J., Bazureau J P., Tetrahedron 2005 61 12386
77. Yadav J S., Reddy B V. S., Basak A K., Narsaiah A V., Green Chem. 2003 5 60
78. Sobolev A, Franssen M C. R., Vigante B, Cekavicus B, Zhalubovskis R, Kooijman H, Spek A L., Duburs G, deGroot A, J. Org. Chem. 2002 67 401
79. For selected recent papers on the aromatization of 1,4-dihydropyridines, see:, Peng L.-J, Wang J.-T, Lu Z, Liu Z.-Q, Wu L.-M, Tetrahedron Lett. 2008 49 1586
80. Filipan-Litvic M, Litvic M, Vinkovic V, Bioorg. Med. Chem. 2008 16 9276
81. Filipan-Litvic M, Litvic M, Vinkovic V, Tetrahedron 2008 64 10912
82. Filipan-Litvic M, Litvic M, Vinkovic V, Tetrahedron 2008 64 5649
83. Heravi M M., Derikvand F, Hassan-Pour S, Bakhtiari K, Bamoharram F F., Oskooie H A., Bioorg. Med. Chem. Lett. 2007 17 3305
84. Fang X, Liu Y.-C, Li C, J. Org. Chem. 2007 72 8608
85. Adibi H, Hajipour A R., Bioorg. Med. Chem. Lett. 2007 17 1008
86. Nasr-Esfahani M, Moghadam M, Tangestaninejad S, Mirkhani V, Momeni A R., Bioorg. Med. Chem. 2006 14 2720
87. Moghadam M, Nasr-Esfahani M, Tangestaninejad S, Mirkhani V, Bioorg. Med. Chem. Lett. 2006 16 2026
88. Han B, Liu Z, Liu Q, Yang L, Liu Z.-L, Yu W, Tetrahedron 2006 62 2492
89. Chai L, Zhao Y, Sheng Q, Liu Z.-Q, Tetrahedron Lett. 2006 47 9283
90. Zolfigol M A., Choghamarani A G., Shahamirian M, Safaiee M, Mohammadpoor-Baltork I, Mallakpour S, Abdollahi-Alibeik M, Tetrahedron Lett. 2005 46 5581
91. Nasr-Esfahani M, Moghadam M, Tangestaninejad S, Mirkhani V, Bioorg. Med. Chem. Lett. 2005 15 3276
92. Heravi M M., Behbahani F K., Oskooie H A., Shoar R H., Tetrahedron Lett. 2005 46 2775
93. Han B, Liu Q, Liu Z, Mu R, Zhang W, Liu Z.-L, Yu W, Synlett 2005 2333
94. Nakamichi N, Kawashita Y, Hayashi M, Org. Lett. 2002 4 3955
95. Mao Y.-Z, Jin M.-Z, Liu Z.-L, Wu L.-M, Org. Lett. 2000 2 741
96. For selected recent reviews on the synthesis of pyridines using enamines, see:, Stanovnik B, Svete J, Chem. Rev. 2004 104 2433
97. Erian A W., Chem. Rev. 1993 93 1991
98. For selected recent papers on the synthesis of pyridines using enamines, see:, Ravinder M, Sadhu P S., Rao V J., Tetrahedron Lett. 2009 50 4229
99. Nakaike Y, Hayashi D, Nishiwaki N, Tobe Y, Ariga M, Org. Biomol. Chem. 2009 7 325
100. Chen Z.-B, Hong D, Wang Y.-G, J. Org. Chem. 2009 74 903
101. Cacchi S, Fabrizi G, Filisti E, Org. Lett. 2008 10 2629
102. Movassaghi M, Hill M D., Ahmad O K., J. Am. Chem. Soc. 2007 129 10096
103. Dondoni A, Massi A, Aldhoun M, J. Org. Chem. 2007 72 7677
104. Bagley M C., Glover C, Chevis D, Synlett 2005 649
105. Bagley M C., Xiong X, Org. Lett. 2004 6 3401
106. Bagley M C., Glover C, Merritt E A., Xiong X, Synlett 2004 811
107. Bagley M C., Hughes D D., Sabo H M., Taylor P H., Xiong X, Synlett 2003 1443
108. Bagley M C., Dale J W., Xiong X, Bower J, Org. Lett. 2003 5 4421
109. Bagley M C., Dale J W., Ohnesorge M, Xiong X, Bower J, J. Comb. Chem. 2003 5 41
110. Adamo M F. A., Adlington R M., Baldwin J E., Pritchard G J., Rathmell R E., Tetrahedron 2003 59 2197
111. Bagley M C., Lunn R, Xiong X, Tetrahedron Lett. 2002 43 8331
112. Bagley M C., Brace C, Dale J W., Ohnesorge M, Phillips N G., Xiong X, Bower J, J. Chem. Soc., Perkin Trans. 1 2002 1663
113. Bagley M C., Dale J W., Hughes D D., Ohnesorge M, Phillips N G., Bower J, Synlett 2001 1523
114. Bagley M C., Dale J W., Bower J, Synlett 2001 1149
115. Sasada T, Sawada T, Ikeda R, Sakai N, Konakahara T, Eur. J. Org. Chem. 2010 4237
116. Sasada T, Moriuchi M, Sakai N, Konakahara T, Eur. J. Org. Chem. 2009 5738
117. Sasada T, Sakai N, Konakahara T, J. Org. Chem. 2008 73 6905
118. Sakai N, Aoki Y, Sasada T, Konakahara T, Org. Lett. 2005 7 4705
119. Sasada T, Kobayashi F, Sakai N, Konakahara T, Org. Lett. 2009 11 2161
120. 4-catalyzed reaction, see:, Sakai N, Shimamura K, Ikeda R, Konakahara T, J. Org. Chem. 2010 75 3923
121. Sakai N, Sato A, Konakahara T, Synlett 2009 1449
122. Nakamura M, Niiyama K, Yamakawa T, Tetrahedron Lett. 2009 50 6462
123. Sakai N, Asano J, Shimano Y, Konakahara T, Tetrahedron 2008 64 9208
124. Wu Y.-C, Zhu J, J. Org. Chem. 2008 73 9522
125. Yoon M Y., Kim J H., Choi D S., Shin U S., Lee J Y., Song C E., Adv. Synth. Catal. 2007 349 1725
126. Sakai N, Asano J, Shimano Y, Konakahara T, Synlett 2007 2675
127. Qin H, Yamagiwa N, Matsunaga S, Shibasaki M, Chem. Asian J. 2007 2 150
128. Noji M, Konno Y, Ishii K, J. Org. Chem. 2007 72 5161
129. Kawatsura M, Aburatani S, Uenishi J, Tetrahedron 2007 63 4172
130. Oohashi Y, Fukumoto K, Mukaiyama T, Chem. Lett. 2005 34 190
131. Oohashi Y, Fukumoto K, Mukaiyama T, Chem. Lett. 2005 34 710
132. Kawatsura M, Aburatani S, Uenishi J, Synlett 2005 2492
133. Song C E., Jun D.-U, Choung S.-Y, Roh E J., Lee S.-G, Angew. Chem. Int. Ed. 2004 43 6183
134. Azumaya I, Kotani M, Ikegami S, Synlett 2004 959
135. Sakai N, Hirasawa M, Hamajima T, Konakahara T, J. Org. Chem. 2003 68 483
136. Hachiya I, Moriwaki M, Kobayashi S, Tetrahedron Lett. 1995 36 409
137. For selected papers on the synthesis of pyridines using enamines and orthoesters, see:, Sagitullina G P., Glizdinskaya L V., Oleinikova S I., Atavin E G., Sagitullin R S., Russ. J. Org. Chem. 2005 41 1367
138. Pyrko A N., Chem. Heterocycl. Compd. 1999 35 688
139. Murray T J., Zimmerman S C., Kolotuchin S V., Tetrahedron 1995 51 635
140. For selected previous papers on the synthesis of enamines, see:, Konakahara T, Takagi Y, Heterocycles 1980 14 393
141. Konakahara T, Kurosaki Y, J. Chem. Res., Synop 1989 130
142. Konakahara T, Watanabe A, Maehara K, Nagata M, Hojahmat M, Heterocycles 1993 35 1171
143. Konakahara T, Sugama N, Yamada A, Kakehi A, Sakai N, Heterocycles 2001 55 313
144. Konakahara T, Ogawa R, Tamura S, Kakehi A, Sakai N, Heterocycles 2001 55 1737
145. Konakahara T, Hojahmat M, Tamura S, J. Chem. Soc., Perkin Trans. 1 1999 2803
146. Hojhamat M, Konakahara T, Tamura S, Heterocycles 2000 53 629
147. Konakahara T., Sato K., Bull. Chem. Soc. Jpn. 1983 56 1241
148. Person R G., J. Chem. Educ. 1968 45 581
149. Yamamoto Y, J. Org. Chem. 2007 72 7817