Endo-Mode cyclizations of vinylogous N-acyliminium ions as a route to the synthesis of condensed thiazolidines

Tetrahedron

Volumn 67, Issue 49, 2011, Pages 9541-9554

  Stojanović, Milovan ^a,b   Marković, Rade ^a,c   Kleinpeter, Erich ^b   Baranac Stojanović, Marija ^a,b,c  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF POTSDAM   (Germany)

^c UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Condensed thiazolidines; endo Mode cyclization; Quantum chemical calculations; Vinylogous N acyliminium ion

Indexed keywords

4 OXOTHIAZOLIDINE DERIVATIVE; ETHYL 2 (4 OXOTHIAZOLIDIN 2 YLIDENE)ACETATE; ETHYL 2 (5 METHYL 4 OXOTHIAZOLIDIN 2 YLIDENE)ACETATE; IMINE; N ACYLIMINIUM; NUCLEOPHILE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; QUANTUM CHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 80555122817     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.011     Document Type: Article

References (78)

1. M. Tramontini Synthesis 1973 703
2. B. Reichert Die Mannich Reaktion 1959 Springer Berlin
3. F.F. Blicke Org. React. 1 1942 303
4. E.D. Cox, and J.M. Cook Chem. Rev. 95 1995 1797
5. For a review on iminium ions, see: J. Royer, M. Bonin, and L. Micouin Chem. Rev. 104 2004 2311 for reviews on N-acyliminium ions, see
6. B.E. Maryanoff, H.-C. Zhang, J.H. Cohen, I.J. Turchi, and C.A. Maryanoff Chem. Rev. 104 2004 1431
7. W.N. Speckamp, and M.J. Moolenaar Tetrahedron 56 2000 3817 for selected examples, see
8. F.D. King, A.E. Aliev, S. Caddick, D.A. Tocher, and D. Courtier-Murias Org. Biomol. Chem. 7 2009 167
9. C. Li, X. Li, and R. Hong Org. Lett. 11 2009 4036
10. Y. Tang, C. Fettinger, and J.T. Shaw Org. Lett. 11 2009 3802
11. B.J. Min, X. Gu, T. Yamamoto, R.R. Petrov, H. Qu, Y.S. Lee, and V.J. Hruby Tetrahedron Lett. 49 2008 2316
12. A.W. Pilling, J. Boehmer, and D.J. Dixon Angew. Chem., Int. Ed. 46 2007 5428
13. W.-H. Chiou, N. Mizutani, and I. Ojima J. Org. Chem. 72 2007 1871
14. T.E. Nielsen, S. Le Quement, and M. Meldal Org. Lett. 7 2005 3601
15. J.E. Baldwin J. Chem. Soc., Chem. Commun. 1976 734
16. J.E. Baldwin, J., Cutting, W. Dupont, L. Kruse, L. Silberman, and R.C. Thomas J. Chem. Soc., Chem. Commun. 1976 736
17. For examples, with heteroatom-based nucleophiles, see: S. Yamada, and Y. Takahashi Tetrahedron Lett. 50 2009 5395
18. A.A. Bahajaj, M.H. Moore, and J.M. Vernon Tetrahedron 60 2004 1235
19. A.A. Bahajaj, J.M. Vernon, and G.D. Wilson Tetrahedron 60 2004 1247
20. H. Sun, and K.D. Moeller Org. Lett. 4 2002 1547
21. F. Cornille, Y.M. Fobian, U. Slomczynska, D.D. Beusen, G.R. Marshall, and K.D. Moeller Tetrahedron Lett. 35 1994 6989
22. S. Kobayashi, M. Isobe, and T. Saegusa Bull. Chem. Soc. Jpn. 55 1982 1921
23. J.A.M. Hamersma, P.M.M. Nossin, and W.N. Speckamp Tetrahedron 41 1985 1999
24. J.A.M. Hamersma, and W.N. Speckamp Tetrahedron 38 1982 3255
25. J.A.M. Hamersma, H.E. Schoemaker, and W.N. Speckamp Tetrahedron Lett. 1979 1347
26. J.A.M. Hamersma, and W.N. Speckamp Tetrahedron 41 1985 2861
27. J.A.M. Hamersma, and W.N. Speckamp Tetrahedron Lett. 23 1982 3811
28. D. Fasseur, B. Rigo, P. Cauliez, M. Debacker, and D. Couturier Tetrahedron Lett. 31 1990 1713
29. D.J. Hart J. Org. Chem. 46 1981 367
30. E. Winterfeldt Synthesis 1975 617 Ref. 129
31. R. Marković, M. Baranac, P. Steel, E. Kleinpeter, and M. Stojanović Heterocycles 65 2005 2635
32. R. Marković, M. Baranac, and M. Stojanović Synlett 2004 1034
33. For a selected literature on push-pull alkenes, see: P. Rattananakin, C.R. Pittman Jr., W.E. Collier, and S. Saebø Struct. Chem. 18 2007 399
34. E. Kleinpeter J. Serb. Chem. Soc. 71 2006 1
35. E. Kleinpeter, S. Klod, and W.-D. Rudorf J. Org. Chem. 69 2004 4317
36. J. Sandström Top. Stereochem. 14 1983 83
37. 4 does not reduce esters under ambient conditions. Such reduction is possible under reflux conditions or by enhancing its reactivity by the addition of certain additives. For examples, with additives, see: M. Periasami, and M. Thirumalaikumar J. Organomet. Chem. 609 2000 137
38. A.B.S. Prasad, J.V.B. Kanth, and M. Periassamy Tetrahedron 48 1992 4623
39. T. Yamakawa, M. Masaki, and H. Nohira Bull. Chem. Soc. Jpn. 64 1991 2730 For examples, of using reflux temperature, see
40. J.C.S. da Costa, K.C. Pais, E.L. Fernandes, P.S.M. de Oliveira, J.S. Mendona, M.V.N. de Souza, M.A. Peralta, and T.R.A. Vasconcelos Arkivoc i 2006 128
41. N. Boechat, J.C.S. da Costa, J.S. Mendona, P.S.M. de Oliveira, and M.V.N. de Souza Tetrahedron Lett. 45 2004 6021
42. 4 thereby activating it. For examples, see
43. A. Patra, S. Batra, and A.P. Bhaduri Synlett 2003 1611
44. J. Kim, K.A. De Castro, M. Lim, and H. Rhee Tetrahedron 66 2010 3995
45. R. Marković, M. Baranac, V. Jovanović, and Z. Džambaski J. Chem. Educ. 81 2004 1026
46. R. Marković, M. Baranac, Z. Džambaski, M. Stojanović, and P.J. Steel Tetrahedron 59 2003 7803 The synthesis of 7a and 7b was not published previously, by us
47. For the determination of configuration around the carbon-carbon double bond in these and similar compounds, and isomerization studies, see: R. Marković, M. Baranac, N. Juranić, S. Macura, I. Cekić, and D. Minić J. Mol. Struct. 800 2006 85
48. R. Marković, A. Shirazi, Z. Džambaski, M. Baranac, and D. Minić J. Phys. Org. Chem. 17 2004 118
49. R. Marković, Z. Džambaski, and M. Baranac Tetrahedron 57 2001 5833
50. R. Marković, and M. Baranac Heterocycles 48 1998 893 and Ref 14 in the present paper
51. Some endo-mode cyclizations have been communicated: M. Stojanović, and R. Marković Synlett 2009 1997
52. H.V. Geluk, and J.L.M.A. Schlatmann Tetrahedron 24 1968 5361
53. T.-C. Zheng, M. Burkart, and D.E. Richardson Tetrahedron Lett. 40 1999 603
54. J.H. Van Maarseveen, H.W. Scheeren, and C.G. Kruse Tetrahedron 49 1993 2325
55. M.S. Yu, I. Lantos, Z.-Q. Peng, J. Yu, and T. Cacchio Tetrahedron Lett. 41 2000 5647
56. J. Marco-Contelles, and M. Rodrígues-Fernándes J. Org. Chem. 66 2001 3717
57. S.G. Alvarez, and M.T. Alvarez Synthesis 1997 413
58. B. Pal, P. Jaisankar, and V.S. Giri Synth. Commun. 34 2004 1317
59. J.C. Hubert, J.B.P.A. Wijnberg, and W.N. Speckamp Tetrahedron 31 1975 1437
60. Similar dehydration, which slows down or completely blocks the cyclization, has also been observed in reactions starting from imidazolidin-2-ones and thiazolidin-2-ones as iminium ion precursors. For examples, see: Z.K. Liao, and K. Kohn J. Org. Chem. 49 1984 4745
61. K. Kohn, and Z.K. Liao J. Org. Chem. 47 1982 2787 and Refs. 6b and 6c in the present paper
62. M. Baranac-Stojanović, and E. Kleinpeter J. Org. Chem. 76 2011 3861
63. A.D. Becke J. Chem. Phys. 98 1993 5648
64. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B: Condens. Matter 37 1988 785
65. M. Cossi, V. Barone, R. Cammi, and J. Tomasi Chem. Phys. Lett. 255 1996 327
66. B. Mennucci, and J. Tomasi J. Chem. Phys. 106 1997 5151
67. Y. Yamamoto, T. Nakada, and H. Nemoto J. Am. Chem. Soc. 114 1992 121
68. 1H NMR spectrum of the isolated product 18d after several months standing in a freezer, yielding a mixture trans/cis 73/28.
69. R. Karaman Bioorg. Chem. 38 2010 165 and references cited therein
70. R. Karaman Tetrahedron Lett. 49 2008 5998 and references cited therein
71. A.E. Reed, and F. Weinhold J. Chem. Phys. 83 1985 1736
72. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735
73. A.E. Reed, and F. Weinhold J. Chem. Phys. 78 1983 4066
74. J.P. Foster, and F. Weinhold J. Am. Chem. Soc. 102 1980 7211
75. N. Taxak, V. Parmar, D.S. Patel, A. Kotasthane, and P.V. Bharatam J. Phys. Chem. A 115 2011 891
76. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennuci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Babuol, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzales, and J.A. Pople Gaussian 03 (Revision C.02) 2004 Gaussian Wallingford CT
77. G. Satzinger Liebigs Ann. Chem. 665 1963 150
78. O. Ceder, U. Stenhede, K.-I. Dahlquist, J.M. Waisvisz, and M.G. van der Hoeven Acta Chem. Scand. 27 1973 1914