Retro-Claisen condensation versus pyrrole formation in reactions of amines and 1,3-diketones

Tetrahedron Letters

Volumn 51, Issue 22, 2010, Pages 2945-2947

  Deb, Indubhusan ^a   Seidel, Daniel ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIKETONE; ACETOPHENONE; ACETYLACETONE; AMINE; BETA CARBOLINE; ENAMINONE; N BENZOYL PYRROLIDINONE; N,O ACETAL; PYRROLE DERIVATIVE; PYRROLIDINE; TETRAHYDROISOQUINOLINE; UNCLASSIFIED DRUG; XYLENE;

ARTICLE; CHEMICAL REACTION KINETICS; CLAISEN CONDENSATION; COLUMN CHROMATOGRAPHY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE IRRADIATION; OXIDATION REDUCTION REACTION; REACTION TIME;

EID: 77951253715     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.086     Document Type: Article

References (90)

1. K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The Porphyrin Handbook, Synthesis and Organic Chemistry, Vol. 1, 2000, p 405.
2. Hoffmann H., and Lindel T. Synthesis (2003) 1753
3. Fuerstner A. Angew. Chem., Int. Ed. 42 (2003) 3582
4. Gupton J.T. Top. Heterocycl. Chem. 2 (2006) 53
5. Walsh C.T., Garneau-Tsodikova S., and Howard-Jones A.R. Nat. Prod. Rep. 23 (2006) 517
6. Fan H., Peng J., Hamann M.T., and Hu J.-F. Chem. Rev. 108 (2008) 264
7. Forte B., Malgesini B., Piutti C., Quartieri F., Scolaro A., and Papeo G. Mar. Drugs 7 (2009) 705
8. Curran D., Grimshaw J., and Perera S.D. Chem. Soc. Rev. 20 (1991) 391
9. Sessler J.L., and Weghorn S.J. Expanded, Contracted & Isomeric Porphyrins (1997), Elsevier Science Ltd, Oxford
10. Gribble G.W. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 2 (1996), Pergamon Press, Oxford 207
11. Bellina F., and Rossi R. Tetrahedron 62 (2006) 7213
12. For classical approaches to pyrroles, see:. Knorr L. Ber. Dtsch. Chem. Ges. 17 (1884) 1635
13. Pall C. Ber. Dtsch. Chem. Ges. 18 (1885) 367
14. Hantzsch A. Ber. Dtsch. Chem. Ges. 23 (1890) 1474
15. For selected reviews, see:. Balme G. Angew. Chem., Int. Ed. 43 (2004) 6238
16. Schmuck C., and Rupprecht D. Synthesis (2007) 3095
17. Patil N.T., and Yamamoto Y. ARKIVOC (2007) 121
18. For selected recent pyrrole syntheses, see:. Gorin D.J., Davis N.R., and Toste F.D. J. Am. Chem. Soc. 127 (2005) 11260
19. Martin R., Rivero M.R., and Buchwald S.L. Angew. Chem. Int. Ed. 45 (2006) 7079
20. Binder J.T., and Kirsch S.F. Org. Lett. 8 (2006) 2151
21. St. Cyr D.J., and Arndtsen B.A. J. Am. Chem. Soc. 129 (2007) 12366
22. Milgram B.C., Eskildsen K., Richter S.M., Scheidt W.R., and Scheidt K.A. J. Org. Chem. 72 (2007) 3941
23. Bergner I., and Opatz T. J. Org. Chem. 72 (2007) 7083
24. Istrate F.M., and Gagosz F. Org. Lett. 9 (2007) 3181
25. Hinze C., Kreipl A., Terpin A., and Steglich W. Synthesis (2007) 608
26. Lu Y., and Arndtsen B.A. Angew. Chem., Int. Ed. 47 (2008) 5430
27. Bremner W.S., and Organ M.G. J. Comb. Chem. 10 (2008) 142
28. Khalili B., Jajarmi P., Eftekhari-Sis B., and Hashemi M.M. J. Org. Chem. 73 (2008) 2090
29. Chiba S., Wang Y.-F., Lapointe G., and Narasaka K. Org. Lett. 10 (2008) 313
30. Lu Y., Fu X., Chen H., Du X., Jia X., and Liu Y. Adv. Synth. Catal. 351 (2009) 129
31. Pahadi N.K., Paley M., Jana R., Waetzig S.R., and Tunge J.A. J. Am. Chem. Soc. 131 (2009) 16626
32. Bergner I., Wiebe C., Meyer N., and Opatz T. J. Org. Chem. 74 (2009) 8243
33. Aponick A., Li C.-Y., Malinge J., and Marques E.F. Org. Lett. 11 (2009) 4624
34. Merkul E., Boersch C., Frank W., and Muller T.J.J. Org. Lett. 11 (2009) 2269
35. Ackermann L., Sandmann R., and Kaspar L.T. Org. Lett. 11 (2009) 2031
36. Liang M., Saiz C., Pizzo C., and Wipf P. Tetrahedron Lett. 50 (2009) 6810
37. Maiti S., Biswas S., and Jana U. J. Org. Chem. 75 (2010) 1674
38. Zhang C., De C.K., Mal R., and Seidel D. J. Am. Chem. Soc. 130 (2008) 416
39. Murarka S., Zhang C., Konieczynska M.D., and Seidel D. Org. Lett. 11 (2009) 129
40. Zhang C., Murarka S., and Seidel D. J. Org. Chem. 74 (2009) 419
41. Murarka S., Deb I., Zhang C., and Seidel D. J. Am. Chem. Soc. 131 (2009) 13226
42. Zhang C., and Seidel D. J. Am. Chem. Soc. 132 (2010) 1798
43. For other selected examples of redox-neutral amine α-functionalizations, see:. Ten Broeke J., Douglas A.W., and Grabowski E.J.J. J. Org. Chem. 41 (1976) 3159
44. Verboom W., Reinhoudt D.N., Visser R., and Harkema S. J. Org. Chem. 49 (1984) 269
45. De Boeck B., Jiang S., Janousek Z., and Viehe H.G. Tetrahedron 50 (1994) 7075
46. Meth-Cohn O. Adv. Heterocycl. Chem. 65 (1996) 1
47. Pastine S.J., McQuaid K.M., and Sames D. J. Am. Chem. Soc. 127 (2005) 12180
48. Matyus P., Elias O., Tapolcsanyi P., Polonka-Balint A., and Halasz-Dajka B. Synthesis (2006) 2625
49. Ryabukhin S.V., Plaskon A.S., Volochnyuk D.M., Shivanyuk A.N., and Tolmachev A.A. J. Org. Chem. 72 (2007) 7417
50. Ryabukhin S.V., Plaskon A.S., Volochnyuk D.M., Shivanyuk A.N., and Tolmachev A.A. Synthesis (2007) 2872
51. Indumathi S., Kumar R.R., and Perumal S. Tetrahedron 63 (2006) 1411
52. Oda M., Fukuchi Y., Ito S., Thanh N.C., and Kuroda S. Tetrahedron Lett. 48 (2007) 9159
53. Belskaia N.P., Deryabina T.G., Koksharov A.V., Kodess M.I., Dehaen W., Lebedev A.T., and Bakulev V.A. Tetrahedron Lett. 48 (2007) 9128
54. Barluenga J., Fananas-Mastral M., Aznar F., and Valdes C. Angew. Chem., Int. Ed. 47 (2008) 6594
55. Polonka-Balint A., Saraceno C., Ludányi K., Bényei A., and Matyus P. Synlett (2008) 2846
56. Che X., Zheng L., Dang Q., and Bai X. Synlett (2008) 2373
57. Zheng L., Yang F., Dang Q., and Bai X. Org. Lett. 10 (2008) 889
58. Mori K., Ohshima Y., Ehara K., and Akiyama T. Chem. Lett. 38 (2009) 524
59. Ruble J.C., Hurd A.R., Johnson T.A., Sherry D.A., Barbachyn M.R., Toogood P.L., Bundy G.L., Graber D.R., and Kamilar G.M. J. Am. Chem. Soc. 131 (2009) 3991
60. 3 C-H bonds adjacent to nitrogen in heterocycles, see:. Campos K.R. Chem. Soc. Rev. 36 (2007) 1069
61. Soeder R.W., Bowers K., Pegram L.D., and Cartaya-Marin C.P. Synth. Commun. 22 (1992) 2737
62. For other selected syntheses of fused pyrroles, see:. Hershenson F.M. J. Org. Chem. 40 (1975) 740
63. Anderson W.K., and Corey P.F. J. Med. Chem. 20 (1977) 812
64. Barluenga J., Tomas M., Kouznetsov V., Suarez-Sobrino A., and Rubio E. J. Org. Chem. 61 (1996) 2185
65. Katritzky A.R., Fali C.N., and Li J. J. Org. Chem. 62 (1997) 4148
66. Dieter R.K., and Yu H. Org. Lett. 2 (2000) 2283
67. Rajaraman S., and Jimenez L.S. Tetrahedron 58 (2002) 10407
68. Reisser M., and Maas G. J. Org. Chem. 69 (2004) 4913
69. Kim J.T., and Gevorgyan V. J. Org. Chem. 70 (2005) 2054
70. Nyerges M., and Toke L. Tetrahedron Lett. 46 (2005) 7531
71. Harrison T.J., Kozak J.A., Corbella-Pane M., and Dake G.R. J. Org. Chem. 71 (2006) 4525
72. Espenlaub S., Gerster H., and Maas G. ARKIVOC (2007) 114
73. Su S., and Porco Jr. J.A. J. Am. Chem. Soc. 129 (2007) 7744
74. Bissember A.C., Phillis A.T., Banwell M.G., and Willis A.C. Org. Lett. 9 (2007) 5421
75. Hulcoop D.G., and Lautens M. Org. Lett. 9 (2007) 1761
76. Toth J., Nedves A., Dansco A., Blasko G., Toke L., and Nyerges M. Synthesis (2007) 1003
77. Hwang S.J., Cho S.H., and Chang S. J. Am. Chem. Soc. 130 (2008) 16158
78. Peng Y., Yu M., and Zhang L. Org. Lett. 10 (2008) 5187
79. Raheem I.T., Thiara P.S., and Jacobsen E.N. Org. Lett. 10 (2008) 1577
80. Fu X., Chen J., Li G., and Liu Y. Angew. Chem., Int. Ed. 48 (2009) 5500
81. Huang X., Zhu S., and Shen R. Adv. Synth. Catal. 351 (2009) 3118
82. Wood K., Black D.S., and Kumar N. Tetrahedron Lett. 50 (2009) 574
83. Tucker J.W., Narayanam J.M.R., Krabbe S.W., and Stephenson C.R. J. Org. Lett. 12 (2010) 368
84. Voskressensky, L. G.; Listratova, A. V.; Bolshov, A. V.; Bizhko, O. V.; Borisova, T. N.; Varlamov, A. V. Tetrahedron Lett. 51, 840.
85. Nunes C.M., Silva M.R., Beja A.M., Fausto R., and Pinho e Melo T.M.V.D. Tetrahedron Lett. 51 (2010) 411
86. Indium triflate catalyzed retro-Claisen condensations between β-diketones and alcohols were recently described by Kuninobu and Takai, who also reported the formation of N-acyl morpholine from acetylacetone and morpholine:. Kawata A., Takata K., Kuninobu Y., and Takai K. Angew. Chem., Int. Ed. 46 (2007) 7793
87. 13C NMR) and analytical data.
88. +.
89. +.
90. +.