Cycloaddition reactions of cross-conjugated enaminones

Tetrahedron

Volumn 65, Issue 41, 2009, Pages 8478-8485

  Singh, Parvesh ^a   Sharma, Parul ^a   Bisetty, Krishna ^a   Mahajan, Mohinder P ^b  

^a DURBAN UNIVERSITY OF TECHNOLOGY   (South Africa)

^b GURU NANAK DEV UNIVERSITY   (India)

Author keywords

Cross conjugated enaminones; Cycloaddition reactions; DMAD; Ketenes

Indexed keywords

2 PYRONE DERIVATIVE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ACRYLIC ACID DERIVATIVE; ENAMINE; KETENE DERIVATIVE; PYRAN DERIVATIVE; PYRROLE DERIVATIVE; REAGENT; THIOPYRAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONJUGATION; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 69549096058     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.038     Document Type: Article

References (80)

1. Radwan S.M., Bakhite E.A., and Kamal El-Dean A.M. Phosphorus, Sulfur Silicon Relat. Elem. 101 (1995) 207-211
2. Wang W., Shimo T., Hashimoto H., and Somekawa K. Tetrahedron 63 (2007) 12367-12372
3. Kranjc K., and Kocevar M. Tetrahedron 64 (2008) 45-52
4. Zhao W.G., and Hua R. Tetrahedron 63 (2007) 11803-11808
5. Rousset S., Abarbri M., Thibonnet J., Parrain J.L., and Duchene A. Tetrahedron Lett. 44 (2003) 7633-7636
6. Downs J.R., Grant S.P., Townsend J.D., Schady D.A., Pastine S.J., Embree M.C., Metz C.R., Pennington W.T., Bailey Walsch R.D., and Beam C.F. Can. J. Chem. 82 (2004) 659-664
7. Gerus I.I., Tolmachova N.A., Vdovenko S.I., Froehlich R., and Haufe G. Synthesis 8 (2005) 1269-1278
8. Hegde S.G., and Jones C.R. J. Heterocycl. Chem. 30 (1993) 1501-1508
9. Stuyter M.A.T., Pandit U.K., Speckaamp W.N., and Huismon H.O. Tetrahedron Lett. 3 (1966) 87-90
10. Derbyshire P.A., Hunter G.A., Mcnab M., and Monahan L.C. J. Chem. Soc., Perkin Trans. 1 (1993) 2017-2025
11. Braibante M.E.F., Braibante H.S., Missio L., and Andricopula A. Synthesis (1994) 898-900
12. Singh K., Singh J., and Singh H. Tetrahedron 54 (1998) 935-942
13. Al-Omran F., Al-Awadi N., Abdel-Khalik M.M., Kaul K., El-Khair A.A., and Elnagdi M.H. J. Chem. Res., Synop. 38 (1997) 8401-8445
14. Al-Omran F., Al-Awadi N., El-Khair A.A., and Elnagdi M.H. Org. Prep. Proced. Int. 29 (1997) 285-292
15. Satyanarayana J., Ila H., and Junjappa H. Synthesis 10 (1991) 889-890
16. Hasenknopf B., and Lehn J.-M. Helv. Chim. Acta 79 (1996) 1643-1650
17. Livoreil A., Sauvage J.-P., Armaroli N., Balzani V., Flamigni L., and Ventura B. J. Am. Chem. Soc. 119 (1997) 12114-12124
18. Kepe V., Kocevar M., and Polanc S. J. Heterocycl. Chem. 33 (1996) 1707-1710
19. Strah S., and Stanovnik B. J. Heterocycl. Chem. 34 (1997) 263-267
20. Blache Y., Chavignon O., Sinibaldi M.E., Troin A., Gueiffier A., Teulade J.C., Troin Y., and Gramain J.C. Heterocycles 38 (1994) 1241-1248
21. San Martin R., de Marigorta E.M., and Dominguez E. Tetrahedron 50 (1994) 2255-2264
22. Bartoli G., Cimarelli C., and Palmieri G. J. Chem. Soc., Perkin Trans. 1 (1994) 537-543
23. Tabakovic I. Electrochim. Acta 40 (1995) 2809-2813
24. Dominguez E., Ibeas E., de Maigorta E.M., Palacios J.K., and SanMartin R. J. Org. Chem. 61 (1996) 5435-5439
25. Vogt, B. R. U.S. Patent 4,112,098, 1978; (CA 92: 146801).
26. Kohn E.C., and Liotta A. J. Natl. Cancer Inst. 82 (1990) 54-61
27. Nielsen F.E., Pedersen E.B., and Begtrip M. Liebigs Ann. Chem. 11 (1984) 1848-1859
28. Meier, R. Eur. Patent Appl. EP229, 011, 1987; (CA 107: 198336h).
29. Biagi G., Ferreti M., Livi O., Scartoni V., Lucacchini A., and Mazzoni M. Farmaco Ed. Sci. 41 (1986) 388-400
30. Parlok J.J. J. Heterocycl. Chem. 35 (1998) 1493-1499
31. Frinkelstein B.L., and Strok C.J. J. Pesticide Sci. 50 (1997) 324-332
32. Schallner, O.; Heinz, K. -H.; Karl, K. -J. Ger. Offen DE. 1997, 19615259;
33. Chem. Abstr. 127 (1997) 346387
34. Daidone G., Maggio B., Plescia S., Raffa D., Musiu C., Milia C., Perra G., and Marongiu M.E. Eur. J. Med. Chem. 33 (1998) 375-382
35. Tsuji K., Nakamurana K., Konishi N., Tojo T., Ochi T., Scnoh H., and Masuo M. Chem. Pharm. Bull. 45 (1997) 987-995
36. Nauduri D., and Reddy G. Chem. Pharm. Bull. 46 (1998) 1254-1260
37. Gajare A.S., Bhawsar S.B., and Shingare M.S. Indian J. Chem. 6 (1997) 321-322
38. Wise L.D., Butler D.E., Dewald H.A., Lustgarten D.M., Pattison I.C., Schweiss D.N., Coughenour L.L., Downs D.A., Heffner T.G., and Pugsley T.A. J. Med. Chem. 30 (1987) 1807-1812
39. Brune K. Med. Toxicol. 1 (1986) 1-9
40. Olivera R., SanMartin R., and Dominguez E. J. Org. Chem. 65 (2000) 7010-7019
41. Bargagna A., Schenone P., Bondavalli F., and Longobardi M. J. Heterocycl. Chem. 19 (1982) 257-261
42. Singh P., Bisetty K., and Mahajan M.P. S. Afr. J. Chem. 62 (2009) 47-55
43. Kinzel O.D., Ball R.G., Donghi M., Maguire C.K., Muraglia E., Pesci S., Rowley M., and Summa V. Tetrahedron Lett. 49 (2008) 6556-6558
44. Ram R.N., and Kumar N. Tetrahedron 64 (2008) 10267-10271
45. Katoh N., Nakahata T., and Kuwahara S. Tetrahedron 64 (2008) 9073-9077
46. González-Gómez A., Domínguez G., Amador U., and Pérez-Castells J. Tetrahedron Lett. 49 (2008) 5467-5470
47. Nair V., Babu B.P., Varghese V., Sinu C.R., Paul R.R., Anabha E.R., and Suresh E. Tetrahedron Lett. 50 (2009) 3716-3718
48. Terzidis M.A., Dimitriadou E., Tsoleridis C.A., and Stephanidou-Stephanatou J. Tetrahedron Lett. 50 (2009) 2174-2176
49. Case D.A., Darden T.A., Cheatham T.E., Simmerling C.L., Wang J., Duke R.E., Luo R., Merz K.M., Pearlman D.A., Crowley M., Walker R.C., Zhang W., Wang B., Hayik S., Roitberg A., Seabra G., Wong K.F., Paesani F., Wu X., Brozell S., Tsui V., Gohlke H., Yang L., Tan C., Mongan J., Hornak V., Cui G., Beroza P., Mathews D.H., Schafmeister C., Ross W.S., and Kollman P.A. AMBER 9 (2006), University of California, San Francisco
50. Geldenhuys W.J., Malan S.F., Bloomquist J.R., Marchand A.P., and Vander Schyf C.J. Med. Res. Rev. 25 (2005) 21-48
51. Corcho F.J., Filizola M., and Perez J.J. J. Biomol. Struct. Dyn. 16 (1999) 1043-1052
52. Leach A.R. Molecular Modelling: Principles and Applications (1996), Addison Wesley Longman, Essex, UK pp 413-436
53. Lybrand T.P. In: Lipkowitz K.B., and Boyd D.B. (Eds). Reviews in Computational Chemistry Vol. 1 (1990), VCH, New York, NY 295-320
54. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B.C., Pomelli C., Adamo S., Clifford, Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavchari K., Foresman J.B., Cioslowski J., Ortiz J.V., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M.P., Gill M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98, Revision A.3 (1998), Gaussian, Pittsburgh, PA
55. Elnagdi M.H., Mousawi S.M., Abdel-Khalik M.M., El-Sheriny S., and John E. J. Heterocycl. Chem. 38 (2001) 949
56. Jayakumar S., Singh P., and Mahajan M.P. Tetrahedron 60 (2004) 4315-4324
57. Jayakumar S., Ishar M.P.S., and Mahajan M.P. Tetrahedron 58 (2002) 379-471
58. Mohan C., Singh P., and Mahajan M.P. Tetrahedron 61 (2005) 10774-10780
59. Singh P., Marwaha A., Singh H., and Mahajan M.P. Tetrahedron 61 (2005) 11999-12005
60. Abbiati G., Contini A., Nava D., and Rossi E. Tetrahedron 65 (2009) 4664-4670
61. Ibnusaud I., Padma Malar E.J., and Sundaram N. Tetrahedron Lett. 31 (1990) 7357-7358
62. Mazumdar S.N., Ibnusaud I., and Mahajan M.P. Tetrahedron Lett. 29 (1988) 921-924
63. Singh S.P., Mahajan A.R., Prajapati D., and Sandhu J.S. Synthesis (1991) 1026-1028
64. Mazumdar S.N., and Mahajan M.P. Tetrahedron 47 (1991) 1473-1484
65. Mazumdar S.N., Mukherjee S., Sharma A.K., Sengupta D., and Mahajan M.P. Tetrahedron 50 (1994) 7579-7587
66. Sharma A.K., and Mahajan M.P. Heterocycles 40 (1995) 787-800
67. Rossi E., Calabrese D., and Farma F. Tetrahedron 47 (1991) 5819-5834
68. Rossi E., and Pini E. Tetrahedron 52 (1996) 7939-7946
69. Mukherjee S., Mazumdar S.N., Sharma A.K., and Mahajan M.P. Heterocycles 47 (1998) 933-950
70. Rasmussen J.B., Shabana R., and Lawesson S.-O. Tetrahedron 38 (1982) 1705-1709
71. Rasmussen J.B., Shabana R., and Lawesson S.-O. Tetrahedron 37 (1981) 3693-3698
72. Baruah P.D., Mukherjee S., and Mahajan M.P. Tetrahedron 46 (1990) 1951-1962
73. Bogdanowicz-Szwed K., and Budzowski A. Monatsh. Chem. 132 (2001) 947-957
74. Motoki S., Saito T., Karakasa T., Kato H., Matsushita T., and Hayashibe S. J. Chem. Soc., Perkin Trans. 1 (1991) 2281-2283
75. Lecher H.Z., Greenwood R.A., Whitehouse K.C., and Chao T.H. J. Am. Chem. Soc. 78 (1956) 5018-5022
76. Minetto G., Raveglia L.F., Sega A., and Taddei M. Eur. J. Org. Chem. (2005) 5277-5288
77. Scheibye S., Kristensen J., and Lawesson S.-O. Tetrahedron 35 (1979) 1339-1343
78. Brinkmeyer R.S., and Abdullah R.F. Tetrahedron 35 (1979) 1675-1735
79. Accelrys. Materials Studio Release Notes, Release 4.1 (2006), Accelrys Software, San Diego, CA
80. Wang J., Wolf R.M., Caldwell J.W., Kollamn P.A., and Case D.A. J. Comput. Chem. 25 (2004) 1157-1174