Dialkyl Acetone-1,3-Dicarboxylates and their Mono- and bis(Dimethylamino)methylidene Derivatives in the Synthesis of Heterocyclic Systems

Advances in Heterocyclic Chemistry

Volumn 100, Issue , 2010, Pages 145-174

  Stanovnik, Branko ^a   Grošelj, Uroš ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84969751563     PISSN: 00652725     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-2725(10)10005-1     Document Type: Chapter

References (115)

1. Sprague J.M., Lincoln R.M., Ziegler C. J. Am. Chem. Soc. 1946, 68:266.
2. Bodendorf K., Niemeitz P. Arch. Pharm. 1957, 290:494.
3. Hünig S., Köbrich G. J. Liebigs Ann. Chem. 1958, 617:181.
4. Oppolzer W. Tetrahedron Lett. 1970, 3091.
5. Taurand G., Streith J. Tetrahedron Lett. 1972, 2851.
6. Tieckelmann H. Pyridols and Pyridones. Pyridine and Its Derivatives 1974, Supplement Part 3:597. Wiley, New York.
7. T. Y. Shen, R. L. Clark, A. A. Pessolano, B. E. Witzel, and T. J. E. Yanza, German Pat. DE 2.330109 (1974); Chem. Abstr. 80, 95916 (1974).
8. Tserng K.-Y., Bauer L. J. Heterocycl. Chem. 1974, 11:163.
9. Kiehl G., Streith J., Taurand G. Tetrahedron 1974, 30:2851.
10. Seitz G., Kämpchen Th. Arch. Pharm. (Weinheim) 1975, 308:237.
11. Sugiura S., Ohno S., Ohtani O., Izumi K., Kitamikado T., Asai H., Kato K., Hori M., Fujimura H. J. Med. Chem. 1977, 20:80.
12. Gesche P., Klinger F., Streith J., Strub H. Tetrahedron Lett. 1980, 21:4507.
13. Tišler M., Stanovnik B. Comprehensive Heterocyclic Chemistry 1984, Vol. 3:1. Pergamon, Oxford.
14. Brown D.J. Comprehensive Heterocyclic Chemistry 1984, Vol. 3:57. Pergamon, Oxford.
15. Greenhill J.V. Comprehensive Heterocyclic Chemistry 1984, Vol. 5:305. Pergamon, Oxford.
16. Jones G. Comprehensive Heterocyclic Chemistry 1984, Vol. 2:395. Pergamon, Oxford.
17. Elguero J. Comprehensive Heterocyclic Chemistry 1984, Vol. 5:167. Pergamon, Oxford.
18. Gesche P., Klinger F., Müller W., Streith J., Strub H., Sustmann R. Chem. Ber. 1985, 118:4682.
19. Shaffiee A., Ghazar H. J. Heterocycl. Chem. 1986, 23:1171.
20. Smith K., Lindsay C.M., Morris J.K. Chem. Ind. (London) 1988, 302.
21. Donati D., Fusi S., Ponticelli F., Tedeschi P. Heterocycles 1988, 27:1899.
22. B. S. Schober, G. Megyeri, T. Kappe, J. Heterocycl. Chem., 26, 169 (1989).
23. Peters D., Hornfeldt A.-B., Gronowitz S. J. Heterocycl. Chem. 1990, 27:2165.
24. Katner A.S., Brown R.F. J. Heterocycl. Chem. 1990, 27:563.
25. Frank H., Heinisch G. Progress Medicinal Chemistry 1990, Vol. 27:1. Elsevier, Amsterdam.
26. Frank H., Heinisch G. Progress Medicinal Chemistry 1990, Vol. 29:141. Elsevier, Amsterdam.
27. Jelen B., Štimac A., Stanovnik B., Tišler M. J. Heterocycl. Chem. 1991, 28:369.
28. Stanovnik B. Tetrahedron 1991, 47:2925.
29. Molina P., Aller E., Lorenzo A. Tetrahedron 1991, 47:6737.
30. W. J. Michaely, J. K. Curtis, and C. G. Knudsen, US Pat. 5300478, 1994; Chem. Abstr., 121, 57503n (1994).
31. Miyaura H., Suzuki A. Chem. Rev. 1995, 95:2457.
32. Thompson A.M., Bridges A.J., Fry D.W., Kraker A.J., Denny W.A. J. Med. Chem. 1995, 38:3780.
33. Coates W.J. Comprehensive Heterocyclic Chemistry II 1996, Vol. 6:1. Elsevier, Oxford.
34. Elguero J. Comprehensive Heterocyclic Chemistry II 1996, Vol. 3:1. Pergamon, Oxford.
35. Jones G. Comprehensive Heterocyclic Chemistry II. 1996, Vol. 5:167. Elsevier, Oxford.
36. Unheim K., Bennecke.T. Comprehensive Heterocyclic Chemistry II 1996, Vol. 6:93. Elsevier, Oxford.
37. Townsend L.B., Wise D.S. Comprehensive Heterocyclic Chemistry II 2008, Vol. 10:431. Elsevier, Oxford.
38. El Ashry E.S.H., Rashed N. Comprehensive Heterocyclic Chemistry II 1996, Vol. 7:561. Elsevier, Oxford.
39. Stanforth S.P. Comprehensive Heterocyclic Chemistry II. 1996, Vol. 8:345. Elsevier, Oxford.
40. Sliskovic D.R. Comprehensive Heterocyclic Chemistry II 1996, Vol. 8:345. Elsevier, Oxford.
41. Stanovnik B. Methods of Organic Chemistry, Vol. 9a, p. 557 1997, Georg Thieme Verlag, Stuttgart.
42. Gompper R., Mair H., Polborn K. Synthesis 1997, 696.
43. F. Diederich and P. Stang (Eds.), Metal-Catalysed Cross-Coupling Reactions: Wiley VCH, New York (1998).
44. Li J.J., Grible G.W. Palladium in Heterocyclic Chemistry 2000, Pergamon Press, New York.
45. Zupančič S., Svete J., Stanovnik B. Heterocycles 2000, 53:2033.
46. El-Subbagh H.I., Abu-Zaid S.M., Mahran M.A., Badria F.A., Al-Obaid A.M. J. Med. Chem. 2000, 43:2915.
47. Stanovnik B., Svete J. Targ. Heterocycl. Syst. 2000, 4:105.
48. Stanovnik B., Svete J. Synlett 2000, 1077.
49. Hartmaann K.-P., Heuschmann M. Tetrahedron 2000, 56:4213.
50. Chowdhury A.Z.M.S., Shibata Y. Heterocycles 2001, 55:115.
51. Lee K., Jiang M., Cowart M., Gfessar G., Perner R., Kim K.H., Gu Y.G., Williams M., Jarris M.F., Kowaluk E.F., Stewart A.O., Bhagwat S.S. J. Med. Chem. 2001, 44:2133.
52. Contreras J.M., Parrot I., Sippl W., Rival Y., Wermuth C.G. J. Med. Chem. 2001, 44:2707.
53. Tyvorskii V.I., Bobrov D.N., Kulinkovich O.G., Tehrani K.A., De Kimpe N. Tetrahedron 2001, 57:2051.
54. Littke A.F., Fu C.G. Angew. Chem. Int. Ed. 2002, 41:4176.
55. Fukui H., Inoguchi K., Nakano J. Heterocycles 2002, 56:257.
56. Hvala A., Soršak G., Jukić L., Bratušek U., Svete J., Lah N., Leban I., Stanovnik B. Heterocycles 2002, 57:791.
57. Svete J. J. Heterocycl. Chem. 2002, 39:437.
58. Ulrich H., Guilford C.T. Science of Synthesis 2002, Vol. 11:835. Georg Thime Verlag, Stuttgart.
59. Stanovnik B., Svete J. Science of Synthesis 2002, Vol. 12:15. Georg Thieme Verlag, Stuttgart.
60. Hajos G., Riedl Z. Science of Synthesis 2002, Vol. 12:613. Georg Thieme Verlag, Stuttgart.
61. Keller P.A. Science of Synthesis 2002, Vol. 15:285. Georg Thieme Verlag, Stuttgart.
62. Sako M. Pyridopyrimidines. Science of Synthesis 2006, Vol. 16:1155. Thieme Verlag, Stuttgart.
63. Pal M., Batchu V.R., Khanna S., Yeleswarapu K.R. Tetrahedron 2002, 58:9933.
64. Pirc S., Bevk D., Golič Grdadolnik S., Svete J., Stanovnik B. ARKIVOC 2003, xiv:37.
65. Rosoesky A., Chen H., Fu H., Queener S. Bioorg. Med. Chem. 2003, 11:59.
66. Bevk D., Jakše R., Svete J., Golobič A., Golič L., Stanovnik B. Heterocycles 2003, 61:197.
67. Westman J., Lundin R. Synthesis 2003, 1025.
68. Haginoya N., Kobayashi S., Komoriya S., Hirokawa Y., Furugori T., Nagahara T. Bioorg. Med. Chem. Lett. 2004, 14:2935.
69. Zeni G., Larock R.C. Chem. Rev. 2004, 104:2285.
70. Stanovnik B., Svete J. Chem. Rev. 2004, 104:2433.
71. Haginoya N., Komoriya S., Osanai K., Yoshino T., Nagata T., Nagamochi M., Muto R., Yamaguchi M., Nagahara T., Kanno H. Heterocycles 2004, 63:1555.
72. Bevk D., Jakše R., Golobič A., Golič L., Meden A., Svete J., Stanovnik B. Heterocycles 2004, 63:609.
73. Čebašek P., Wagger J., Bevk D., Jakše R., Svete J., Stanovnik B. J. Comb. Chem. 2004, 6:356.
74. Svete J. Monatsh. Chem. 2004, 135:629.
75. Saygili N., Batsanov A.S., Bryce M.R. Org. Biomol. Chem. 2004, 2:852.
76. Susvilo I., Palskite R., Tumkyavitchyus S., Brukshtus A. Chem. Heterocycl. Comp. 2005, 41:268.
77. Bevk D., Golič L., Golobič A., Svete J., Stanovnik B. Heterocycles 2005, 66:207.
78. Svete J. J. Heterocycl. Chem. 2005, 42:361.
79. Stanovnik B., Svete J. Mini-Rev. Org. Chem. 2005, 2:211.
80. Grošelj U., Bevk D., Jakše R., Meden A., Stanovnik B., Svete J. Tetrahedron Asymmetry 2005, 16:2187.
81. Vasilevsky S.F., Mshvidobadze E.V., Mamatyuk V.I., Romanenko G.V., Elguero J. Tetrahedron Lett. 2005, 46:4457.
82. Svete J. ARKIVOC 2006, vii:35.
83. Komoriya S., Kobayashi S., Osanai K., Yoshino T., Nagata T., Haginoya N., Nakamoto Y., Mochizuli A., Nagahara T., Suzuki M., Shimada T., Watanabe K., Isobe Y., Furugori T. Bioorg. Med. Chem. 2006, 14:1309.
84. Zeni G., Larock R.C. Chem. Rev. 2006, 106:4644.
85. Jang M.-Y, De Jonghe S., Gao L.-S., Rozenski J., Herdewijn P. Eur. J. Org. Chem. 2006, 4257.
86. Zupančič S., Svete J., Stanovnik B. Heterocycles 2006, 75:899.
87. Wagger J., Bevk D., Meden A., Svete J., Stanovnik B. Helv. Chim. Acta 2006, 89:240.
88. Čebašek P., Bevk D., Pirc S., Stanovnik B., Svete J. J. Comb. Chem. 2006, 8:95.
89. Nara S., Martinez J., Wermuth C.G., Parrot I. Synlett 2006, 3185.
90. Haider N., Holzer W. Science of Synthesis 2006, 125. Georg Thieme Verlag, Stuttgart. Y. Yamamoto (Ed.).
91. Bevk D., Grošelj U., Meden A., Svete J., Stanovnik B. Tetrahedron 2006, 62:8126.
92. Bevk D., Svete J., Stanovnik B. Heterocycles 2007, 71:657.
93. Bevk D., Grošelj U., Meden A., Svete J., Stanovnik B. Helv. Chim. Acta 2007, 90:1737.
94. Č. Malavašič. B. Brulc, P. Čebašek, G. Dahmann, N. Heine, D. Bevk, U. Grošelj, A. Meden, B. Stanovnik, J. Svete, J. Comb. Chem., 9, 219 (2007).
95. Attanasi O.A., Favi G., Filippone P., Golobič A., Perrulli F.R., Stanovnik B., Svete J. Synlett 2007, 2971.
96. Kralj D., Grošelj U., Meden A., Dahmann G., Stanovnik B., Svete J. Tetrahedron 2007, 63:11213.
97. Grošelj U., Meden A., Stanovnik B., Svete J. Tetrahedron Asymmetry 2007, 18:2365.
98. Grošelj U., Meden A., Stanovnik B., Svete J. Tetrahedron Asymmetry 2007, 18:2746.
99. Wagger J., Grošelj U., Meden A., Stanovnik B., Svete J. Tetrahedron Asymmetry 2007, 18:464.
100. Zupančič S., Svete J., Stanovnik B. Acta Chim. Slov. 2008, 55:1009.
101. S. Zupančič, J. Svete, B. Stanovnik, Acta Chim. Slov., 55, 1019 (2008).
102. Rečnik S., Meden A., Stanovnik B., Svete J. Aust. J. Chem. 2008, 61:107.
103. Buckley B.R. Comprehensive Heterocyclic Chemistry III 1984, Vol. 5:305. Pergamon, Oxford.
104. Regan A.C. Comprehensive Heterocyclic Chemistry III. 2008, Vol. 11:551. Elsevier, Oxford.
105. Yet L. Comprehensive Heterocyclic Chemistry III. 2008, Vol. 4:1. Elsevier, Oxford.
106. Keller P.A. Comprehensive Heterocyclic Chemistry III. 2008, Vol. 7:217. Elsevier, Oxford.
107. Maes B.U.W., Lemiere G.L.F. Comprehensive Heterocyclic Chemistry III 2008, Vol. 8:1. Elsevier, Oxford.
108. Kralj D., Novak A., Dahmann G., Grošelj U., Meden A., Svete J. J. Comb. Chem. 2008, 10:664.
109. Wagger J., Svete J., Stanovnik B. Synthesis 2008, 1436.
110. Wagger J., Grošelj U., Meden A., Svete J., Stanovnik B. Tetrahedron 2008, 64:2801.
111. Grošelj U., Meden A., Stanovnik B., Svete J. Tetrahedron Asymmetry 2008, 19:330.
112. Pahovnik D., Uršič U., Grošelj U., Meden A., Svete J., Stanovnik B. Z. Naturforsch 2008, 63b:407.
113. Žugelj M., Albreht A., Uršič U., Svete J., Stanovnik B. ARKIVOC 2009, vi:137.
114. Baškovč J., Bevk D., Stanovnik B., Svete J. J. Comb. Chem. 2009, 11:500.
115. A. Albreht, U. Uršič, J. Svete, and B. Stanovnik, Heterocycles, 78, 2343 (2009).