Domino routes to substituted benzoindolizines: tandem reorganization of 1,3-dipolar cycloadducts of nitrones with allenic esters/ketones and alternative cycloaddition-palladium catalyzed cyclization pathway

Tetrahedron

Volumn 65, Issue 23, 2009, Pages 4593-4603

  Kapur, Ashish ^a   Kumar, Kamal ^a   Singh, Lakhwinder ^a   Singh, Parminder ^a   Elango, Munusamy ^b   Subramanian, Venkatesan ^b   Gupta, Vivek ^c   Kanwal, Priyanka ^c   Ishar, Mohan Paul S ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

^b CENTRAL LEATHER RESEARCH INSTITUTE   (India)

^c UNIVERSITY OF JAMMU   (India)

Author keywords

Allenic esters; Benzoindolizines; Cycloaddition; Domino routes; Heck reaction

Indexed keywords

1 4 METHOXYBENZYLCARBONYL 3 (2' HYDROXYBENZOYL)BENZO[B]INDOLIZINE; 1 ACETYL 3 (2' HYDROXYBENZOYL) 10 PHENYL BENZO[B]INDOLIZINE; 1 ACETYL 3 (2' HYDROXYBENZOYL)BENZO[B]INDOLIZINE; 1 BENZYLCARBONYL 3 (2' HYDROXYBENZOYL)BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXY 5' CHLORO BENZOYL) 10 METHYL BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXY 5' CHLORO BENZOYL)BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXY 5' CHLOROBENZOYL) 10 ETHYL BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXY 5' FLUOROBENZOYL) 10 ETHYL BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXY 5' FLUOROBENZOYL) 10 METHYL BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXY 5' METHYL BENZOYL) 10 ETHYL BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXY 5' METHYL BENZOYL) 10 METHYL BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXY 5' METHYL BENZOYL)BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXYBENZOYL) 10 ETHYL BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXYBENZOYL) 10 METHYL BENZO[B]INDOLIZINE; 1 ETHOXYCARBONYL 3 (2' HYDROXYBENZOYL)BENZO[B]INDOLIZINE; ALKADIENE; ALKYL GROUP; ESTER DERIVATIVE; ETHER; INDOLIZINE DERIVATIVE; KETONE DERIVATIVE; NITRONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONFORMATION; CONTROLLED STUDY; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; ENERGY YIELD; HECK REACTION; MOLECULAR INTERACTION; ONE POT SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ALNUS;

EID: 65449135868     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.076     Document Type: Article

References (89)

1. Tietze L.F., Brasche G., and Gericke K. Domino Reactions in Organic Synthesis (2006), Wiley-VCH, Weinheim
2. Bunce R.A. Tetrahedron 51 (1995) 13103
3. Tietze L.F. Chem. Rev. 96 (1996) 115
4. Tietze L.F., and Beifuss U. Angew. Chem., Int. Ed. Engl. 32 (1993) 131
5. Tietze L.F. Chem. Ind. (1995) 453
6. Waldmann H. In: Waldmann H. (Ed). Domino Reaction in Organic Synthesis (1995), VCH, Weinheim 193-202
7. Hall N. Science 266 (1994) 32
8. Caruthers W.R. Cycloadditions in Organic Synthesis (1990), Pergamon, London Chapter 6, p 269
9. Black D.C.S., Cozier R.F., and Davis V.C. Synthesis (1975) 205
10. In: Padwa A., Taylor E.C., and Pearson W.H. (Eds). Synthetic Applications of 1,3 Dipolar Cycloadditions Chemistry Towards Heterocycles and Natural Products (2002), Wiley Interscience, New York, NY
11. Paquette L.A. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford Chapter 3
12. Frederickson M. Tetrahedron 53 (1997) 403
13. Gothelf K.V., and Jorgenson K.A. Chem. Rev. 98 (1998) 863
14. Padwa A., and Schoffstall A.M. In: Curran D. (Ed). Advances in Cycloaddition (1990), JAI, Greenwich, CT 2
15. Simonsen K.B., Bayon P., Hazell R.G., Goethelf K.V., and Jorgensen K.A. J. Am. Chem. Soc. 121 (1999) 3845
16. Tamura O., Gotanda K., Yoshino J., Morita Y., Terashima R., Kikuchi M., Miyawaki T., Mita N., Yamashita M., Ishibashi H., and Sakamota M. J. Org. Chem. 65 (2000) 8544
17. Aurich H.G., Geiger M., Gentes C., Harms K., and Koster H. Tetrahedron 54 (1998) 3181
18. Goethelf K.V., Hazell R.G., and Jorgenson K.A. J. Org. Chem. 63 (1998) 5483
19. Chiacchio U., Corsaro A., Iannazzo D., Piperno A., Procopio A., Rescifina A., Romeo G., and Romeo R. J. Org. Chem. 67 (2002) 4380
20. Knobloch K., and Eberbach W. Org. Lett. 2 (2000) 1117
21. Long A., and Baldwin S.W. Tetrahedron Lett. 42 (2001) 5343
22. Voinov M.A., and Grigor'ev I.A. Tetrahedron Lett. 43 (2002) 2445
23. Merino P., Anoro S., Franco S., Merchan F.L., Tejero T., and Tunon V. J. Org. Chem. 65 (2000) 1590
24. Dagoneau C., Tomassini A., Denis J.-N., and Vallee Y. Synthesis (2001) 150
25. Mernyak E., Benedek G., Schneider G., and Wolfling J. Synlett (2005) 637
26. Kanemasa S., Ueno N., and Shirahase M. Tetrahedron Lett. 43 (2002) 657
27. Singh R., Bhella S.S., Sexana A.K., Shanmugavel M., Faruk A., and Ishar M.P.S. Tetrahedron 63 (2007) 2283
28. Singh G., Ishar M.P.S., Gupta V., Singh G., Kalyan M., and Bhella S.S. Tetrahedron 63 (2007) 4773
29. Aouadi K., Vidal S., Msaddek M., and Praly J.-P. Synlett (2006) 3299
30. Aouadi K., Jeanneau E., Msaddek M., and Praly J.-P. Synthesis (2007) 3399
31. Aouadi K., Jeanneau E., Msaddek M., and Praly J.-P. Tetrahedron: Asymmetry 19 (2008) 1145
32. Padwa A., Bullock W.H., Kline D.N., and Perumattam J. J. Org. Chem. 54 (1989) 2862
33. Padwa A., Kline D.N., and Norman B.H. J. Org. Chem. 54 (1989) 810
34. Ishar M.P.S., and Kumar K. Tetrahedron Lett. 40 (1999) 175
35. Two alkaloids containing an indolizine nucleus within a fused ring system have been reported:. Flitsch W. In: Katritzky A.R., and Ress C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 4 (1984), Pergamon, Oxford 476
36. Weidner C.H., Wadsworth D.H., Bender S.L., and Beltman D.J. J. Org. Chem. 54 (1989) 3660
37. Jaung J.Y., and Jung Y.S. Bull. Korean Chem. Soc. 24 (2003) 1565
38. Rotaru A.V., Druta I.D., Oeser T., and Müller T.J.J. Helv. Chim. Acta 88 (2005) 1798
39. Saeva F.D., and Luss H.R. J. Org. Chem. 53 (1988) 1804
40. Delattre F., Woisel P., Surpateanu G., Cazier F., and Blach P. Tetrahedron 61 (2005) 3939
41. Hu J., Jiang X., He T., Zhou J., Hu Y., and Hu H. J. Chem. Soc., Perkin Trans. 1 (2001) 1820
42. Sonnenschein H., Kreher T., Grundemann E., Kruger R.P., Kunath A., and Zabel V. J. Org. Chem. 61 (1996) 710
43. Kel'in A.V., Sromek A.W., and Gevorgyan V. J. Am. Chem. Soc. 123 (2001) 2074
44. Nash R.J., Fellows L.E., Dring J.V., Stirton C.H., Carter D., Hegarty M.P., and Bell E.A. Phytochemistry 27 (1988) 1403
45. Molyneux R.J., and James L.F. Science 216 (1982) 190
46. Okada, S.; Sawada, K.; Kuroda, A.; Watanabe, S.; Tanaka, H. Eur. Pat. Appl. EP 519353, 1992;
47. Chem. Abstr. 118 (1993) 212886y
48. King, F. D.; Gaster, L. M.; Joiner, G. F. PCT Int. Appl. WO 9308187, 1993;
49. Chem. Abstr. 119 (1993) 160281
50. Harrell W.B., and Doerge R.F. J. Pharm. Sci. 56 (1967) 225
51. Harrell W.B. J. Pharm. Sci. 59 (1970) 275
52. Ruprecht R.M., Mullaney S., Anderson J., and Bronson R. J. Acquir. Immune Defic. Syndr. 2 (1989) 149
53. Gruters R.A., Neefjes J.J., Tersmette M., De Goede R.E.Y., Tulp A., Huisman H.G., Miedema F., and Ploegh H.L. Nature 330 (1987) 74
54. Karpas A., Fleet G.W.J., Dwek R.A., Petursson S., Namgoong S.K., Ramsden N.G., Jacob G.S., and Radamacher T.W. Proc. Natl. Acad. Sci. U.S.A. (1989) 86
55. Reddy M.V.R., Rao M.R., Rhodes D., Hansen M.S.T., Rubins K., Bushman F.D., Venkateswarlu Y., and Faulkner D.J. J. Med. Chem. 42 (1999) 1901
56. Humphries M.J., Matsumoto K., White S.L., and Olden K. Cancer Res. 46 (1986) 5215
57. Ostrander G.K., Scribner N.K., and Rohrschneider L.R. Cancer Res. 48 (1988) 1091
58. Lillelund V.H., Jensen H.H., Liang X., and Bols M. Chem. Rev. 102 (2002) 515
59. Pearson W.H., and Guo L. Tetrahedron Lett. 42 (2001) 8267
60. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 1645
61. Anderson W.K., Heider A.R., Raju N., and Yucht J. J. Med. Chem. 31 (1988) 2097
62. Anderson W.K., De Ruiter J., and Heider A.R. J. Org. Chem. 50 (1985) 722
63. Gubin, J.; Descamps, M.; Chatelain, P.; Nisato, D. Eur. Pat. Appl. EP 235111, 1987;
64. Chem. Abstr. 109 (1988) 6405b
65. Gubin J., Vogelaer H., Inion H., Houben C., Lucchetti J., Mahaux J., Rosseels G., Peiren M., Clinet M., Polster P., and Chatelain P. J. Med. Chem. 36 (1993) 1425
66. Gupta S.P., Mathur A.N., Nagappa A.N., Kumar D., and Kumaran S. Eur. J. Med. Chem. 38 (2003) 867
67. Gubin J., Lucchetti J., Mahaux J., Nisato D., Rosseels G., Clinet M., Polster P., and Chatelain P. J. Med. Chem. 35 (1992) 981
68. Rosseels G., Peiren M., Inion H., Deray E., Prost M., Descamps M., Bauthier J., Richard J., Tornay C., Colot M., and Claviere M. Eur. J. Med. Chem. 17 (1982) 581
69. Gundersen L.L., Malterud K.E., Negussie A.H., Rise F., Teklu S., and Østby O.B. Bioorg. Med. Chem. 11 (2003) 5409 and references cited therein
70. Rise, F.; WikstrÕm, H.; Ugland, S.; Dijkstra, D.; Gundersen, L. L.; De Boer, P.; Bast. A.; Haenen, G.; Antonsen, F.; Liao, Y.; Nasir, A. I. PCT Int. Appl. WO 9621, 662/1996;
71. Chem. Abstr. 125 (1996) 195681
72. Oslund R.C., Cermak N., and Gelb M.H. J. Med. Chem. 51 (2008) 4708 and references cited therein
73. Nasir A.I., Gundersen L.L., Rise F., Antonsen F., Kristensen T., Langhelle B., Bast A., Custers L., Haenen G.R.M.M., and Wikstrom H. Bioorg. Med. Chem. Lett. 8 (1998) 1829
74. Østby O.B., Dalhus B., Gundersen L.L., Rise F., Bast A., and Haenen G.R.M.M. Eur. J. Org. Chem. (2000) 3763
75. Kaloko Jr. J., and Hayford A. Org. Lett. 7 (2005) 4305 and references cited therein
76. Liu Y., Song Z., and Yan B. Org. Lett. 9 (2007) 409
77. Smith C.R., Bunnelle E.M., Rhodes A.J., and Sarpong R. Org. Lett. 9 (2007) 1169
78. Chuprakov S., and Gevorgyan V. Org. Lett. 9 (2007) 4463
79. Yan B., and Liu Y. Org. Lett. 9 (2007) 4323
80. Bora U., Saikia A., and Boruah R.C. Org. Lett. 5 (2003) 435
81. Ishar M.P.S., Kumar K., and Singh R. Tetrahedron Lett. 39 (1998) 6547
82. The crystal data of 9f had already been submitted to The Cambridge Crystallographic Data Centre (CCDC No. 285370).
83. Singh G., Singh R., Girdhar N.K., and Ishar M.P.S. Tetrahedron 58 (2002) 2471
84. West R. J. Org. Chem. 23 (1958) 1552
85. Lang R.W., and Hansen H.J. Helv. Chim. Acta 63 (1980) 438
86. Kumar K., Kaur S., and Ishar M.P.S. Synlett (1999) 1237
87. Buono G. Synthesis (1981) 872
88. Nahm S., and Weinreb S.M. Tetrahedron Lett. 22 (1981) 3815
89. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery Jr. 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., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., 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., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98, Revision A.7 (1998), Gaussian, Inc., Pittsburgh, PA