Conjugate additions of o-iodoanilines and methyl anthranilates to acetylenic sulfones. A new route to quinolones including first syntheses of two alkaloids from the medicinal herb Ruta chalepensis

Journal of Organic Chemistry

Volumn 68, Issue 6, 2003, Pages 2223-2233

  Back, Thomas G ^a   Parvez, Masood ^a   Wulff, Jeremy E ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATE ADDITIONS;

ACYLATION; CARBONYLATION; CATALYSTS; ELECTRONS; NEGATIVE IONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ADDITION REACTIONS;

2 IODOANILINE; 4 QUINOLONE DERIVATIVE; ACETYLENE DERIVATIVE; ALKALOID DERIVATIVE; ALLYL SULFONE; ALUMINUM DERIVATIVE; AMALGAM; ANILINE DERIVATIVE; ANTHRANILIC ACID; ANTHRANILIC ACID METHYL ESTER; LITHIUM DERIVATIVE; METHANOL; N FORMYLANILINE; PALLADIUM; RUTA CHALEPENSIS EXTRACT; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL SULFONE;

ACYLATION; ADDITION REACTION; ARTICLE; CATALYSIS; CONJUGATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; ISOMERISM; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ACETYLENE; ALKALOIDS; ANILINE COMPOUNDS; ANTHRANILIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; PLANTS, MEDICINAL; QUINOLONES; RUTA; SULFONES;

EID: 0037459712     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026595t     Document Type: Article

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69. For some reviews of radical cyclization, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986; Chapter 4. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (c) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 4.2. (d) Motherwell, W. B.; Crich, D, Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992, Chapter 7. (e) Malacria, M. Chem. Rev. 1996, 96, 289. (f) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301. (g) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: New York, 1996. (h) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
70. For some reviews of radical cyclization, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986; Chapter 4. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (c) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 4.2. (d) Motherwell, W. B.; Crich, D, Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992, Chapter 7. (e) Malacria, M. Chem. Rev. 1996, 96, 289. (f) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301. (g) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: New York, 1996. (h) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
71. For some reviews of radical cyclization, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986; Chapter 4. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (c) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 4.2. (d) Motherwell, W. B.; Crich, D, Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992, Chapter 7. (e) Malacria, M. Chem. Rev. 1996, 96, 289. (f) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301. (g) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: New York, 1996. (h) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
72. For some reviews of radical cyclization, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986; Chapter 4. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (c) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 4.2. (d) Motherwell, W. B.; Crich, D, Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992, Chapter 7. (e) Malacria, M. Chem. Rev. 1996, 96, 289. (f) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301. (g) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: New York, 1996. (h) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
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74. For other examples of intramolecular acylations of sulfone-stabilized anions, see: (a) Grimm, E. L.; Levac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. (b) Grimm, E. L.; Coutu, M. L. Trimble, L. A. Tetrahedron Lett. 1993, 34, 7017.
75. For other examples of intramolecular acylations of sulfone-stabilized anions, see: (a) Grimm, E. L.; Levac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. (b) Grimm, E. L.; Coutu, M. L. Trimble, L. A. Tetrahedron Lett. 1993, 34, 7017.
76. (a) Omura, S.; Nakagawa, A.; Hashimoto, H.; Oiwa, R.; Iwai, Y.; Hirano, A.; Shibukawa, N.; Kojima, Y. J. Antibiot. 1980, 33, 1395.
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79. Kobayashi, K.; Nakashima, T.; Mano, M.; Morikawa, O.; Konishi, H. Chem. Lett. 2001, 602.
80. Aniline 4d was prepared from methyl anthranilate and benzyl chloroformate, using an identical procedure to that given in ref 31 for the similar protection of 11c.
81. Hays, S. J.; Caprathe, B. W.; Gilmore, J. L.; Amin, N.; Emmerling, M. R.; Michael, W.; Nadimpalli, R.; Nath, R.; Raser, K. J.; Stafford, D.; Watson, D.; Wang, K.; Jaen, J. C. J. Med. Chem. 1998, 41, 1060.
82. Back, T. G.; Bethell, R. J.; Parvez, M.; Taylor, J. A. J. Org. Chem. 2001, 66, 8599.
83. Anthranilic acid was converted into its acyl chloride via the procedure of: Hermecz, I.; Szilagyi, I.; Orfi, L.; Kokosi, J.; Szasz, G. J. Heterocycl. Chem. 1993, 30, 1413. Amide 13 was prepared by reacting the acyl chloride with diethylamine, then protecting with ethyl formate and sodium hydride via the procedure of ref 30.
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85. Methyl 3-iodo-4-aminobenzoate was prepared by a variation of the procedure of: Hill, M. L.; Raphael, R. A. Tetrahedron 1990, 46, 4587. Slow addition of the iodine monochloride reagent to the reaction mixture afforded an improved yield of 95%.
86. Aniline 11b has been previously prepared by a different method, but spectroscopic data was not provided: Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307.
87. Sulfone 9 has been previously prepared by a different method, but spectroscopic data was not provided: Ozawa, M.; Iwata, N.; Kinoshita, H.; Inomata, K. Chem. Lett. 1990, 1689.