Harnessing anionic rearrangements on the benzenoid ring of quinoline for the synthesis of 6,6′-disubstituted 7,7′-dihydroxy-8,8′- biquinolyls

Journal of Organic Chemistry

Volumn 70, Issue 1, 2005, Pages 373-376

  Blakemore, Paul R ^a,b   Kilner, Colin ^a   Milicevic, Selena D ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMERIZATION; OXIDATION; SOLVENTS; SYNTHESIS (CHEMICAL);

BENZENOID RING; DIRECTED ORTHO METALATION (DOM); FERRIC CHLORIDE; HARNESSING ANIONIC REARRANGEMENTS;

ANIONIC POLYMERIZATION;

6,6' BIS DIMETHYLAMINOCARBONYL DIHYDROXYQUINOLYL; 7 DIMETHYL QUINOLYL CARBAMIC ACID; 7,7' DIHYDROXYQUINOLYL; ANION; AROMATIC COMPOUND; CARBAMIC ACID DERIVATIVE; FERRIC CHLORIDE; QUINOLINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANION EXCHANGE; ARTICLE; CHEMICAL STRUCTURE; DIMERIZATION; HALOGENATION; OXIDATION; REACTION ANALYSIS;

EID: 11844278447     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048258l     Document Type: Article

References (49)

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4. Homobimetallic complexes of 1a-c are of interest to us as novel platforms for ambifunctional catalysis. For reviews of ambifunctional catalysis, see: (a) Ma, J.-A.; Cahard, D. Angew. Chem., Int. Ed. 2004, 43, 4566. (b) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989. (c) Rowlands, G. J. Tetrahedron 2001, 57, 1865. (d) Gröger, H. Chem. Eur. J. 2001, 7, 5246. (e) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. 1997, 36, 1236.
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13. 2-hybridized nitrogen-atom lone pairs in analogous 7,7′-dihydroxy-8,8′-biquinolyls. The precise effect that this heteroatom placement will have on configurational stability of the biaryl is unknown; furthermore, various tautomeric forms are available to 6, and each may allow for a different racemization pathway. For a recent high-level computation study of racemization pathways in BINOL, see: Meca, L.; Reha, D.; Havlas, Z. J. Org. Chem. 2003, 68, 5677.
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32. 16b
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36. For halogen-dance reactions on the heterocyclic ring of quinoline derivatives, see: (a) Arzel, E.; Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1999, 55, 12149. (b) Arzel, E.; Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron Lett. 1998, 39, 6465.
37. For selected examples of halogen-dance reactions on heterocycles other than quinoline, see: (a) Sammakia, T.; Stangeland, E. L.; Whitcomb, M. C. Org. Lett. 2002, 4, 2385. (b) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995. (c) Bury, P.; Hareau, G.; Kocienski, P.; Dhanak, D. Tetrahedron 1994, 50, 8793. (d) Fröhlich, H.; Kalt, W. J. Org. Chem. 1990, 55, 2993. (e) Guildford, A.; Tometzki, M. A.; Turner, R. W. Synthesis 1983, 987.
38. For selected examples of halogen-dance reactions on heterocycles other than quinoline, see: (a) Sammakia, T.; Stangeland, E. L.; Whitcomb, M. C. Org. Lett. 2002, 4, 2385. (b) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995. (c) Bury, P.; Hareau, G.; Kocienski, P.; Dhanak, D. Tetrahedron 1994, 50, 8793. (d) Fröhlich, H.; Kalt, W. J. Org. Chem. 1990, 55, 2993. (e) Guildford, A.; Tometzki, M. A.; Turner, R. W. Synthesis 1983, 987.
39. For selected examples of halogen-dance reactions on heterocycles other than quinoline, see: (a) Sammakia, T.; Stangeland, E. L.; Whitcomb, M. C. Org. Lett. 2002, 4, 2385. (b) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995. (c) Bury, P.; Hareau, G.; Kocienski, P.; Dhanak, D. Tetrahedron 1994, 50, 8793. (d) Fröhlich, H.; Kalt, W. J. Org. Chem. 1990, 55, 2993. (e) Guildford, A.; Tometzki, M. A.; Turner, R. W. Synthesis 1983, 987.
40. For selected examples of halogen-dance reactions on heterocycles other than quinoline, see: (a) Sammakia, T.; Stangeland, E. L.; Whitcomb, M. C. Org. Lett. 2002, 4, 2385. (b) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995. (c) Bury, P.; Hareau, G.; Kocienski, P.; Dhanak, D. Tetrahedron 1994, 50, 8793. (d) Fröhlich, H.; Kalt, W. J. Org. Chem. 1990, 55, 2993. (e) Guildford, A.; Tometzki, M. A.; Turner, R. W. Synthesis 1983, 987.
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42. Conversion of 12 to 14 may conceivably be promoted under high dilution conditions. The anionic ortho-Fries rearrangement is an intramolecular process, whereas the equilibrating halogen-dance reaction is an intermolecular chain reaction almost certainly involving N,N-dimethyl O-(6,8-diiodo-7-quinolyl) carbamate as the propagating intermediate.
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46. For Pd(0)-catalyzed thioether formation, see: (a) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651. (b) Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1995, 36, 4133. (c) Migita, T.; Shimizu, T.; Asami. Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385. (d) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron 1997, 53, 1025. (e) Rossi, R.; Bellina, F.; Carpita, A. Synlett 1996, 356. (f) Rajagopalan, S.; Radke, G.; Evans, M.; Tomich, J. M. Synth. Commun. 1996, 26, 1431.
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48. For Pd(0)-catalyzed thioether formation, see: (a) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651. (b) Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1995, 36, 4133. (c) Migita, T.; Shimizu, T.; Asami. Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385. (d) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron 1997, 53, 1025. (e) Rossi, R.; Bellina, F.; Carpita, A. Synlett 1996, 356. (f) Rajagopalan, S.; Radke, G.; Evans, M.; Tomich, J. M. Synth. Commun. 1996, 26, 1431.
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