Synthesis of Cyclo-2,2′:4′,4″:2″,2‴:4‴,4″″: 2″″,2″″′:4″″′,4-sexipyridine

Journal of Organic Chemistry

Volumn 62, Issue 9, 1997, Pages 2774-2781

  Kelly, T Ross ^a   Lee, Yean Jang ^a   Mears, Richard J ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001401952     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962236k     Document Type: Article

References (89)

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50. 3 (37 mL, 0.40 mol) cooled to 5°C, bromine (20.6 mL, 0.40 mol) was introduced dropwise while the mixture was stirred with a glass rod, giving a deep orange solid. To this solid was slowly introduced water (7.2 mL, 0.40 mol) (CARE: EXOTHERMIC), and mixing was continued between additions. The resulting orange slush was transferred to a round-bottomed flask and distilled under vacuum (20 Torr) using a warm condenser (to prevent solidification in and blocking of the condenser). Fractions were collected between 92 and 120°C (head temperature). Yield fraction 1 (<100°C head temperature, 37.7 g, 33%), total yield (98.7 g, 87%). The first fraction collected (<100°C) was a pale orange semisolid and was found to be superior to higher boiling fractions (colorless, crystalline solid mass) for the bromination of pyridone 11.
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72. For examples, see: (a) Kelly, T. R.; Bowyer, M. C.; Bhaskar, K. V.; Bebbington, D.; Garcia, A.; Lang, F.; Kim, M. H.; Jette, M. P. J. Am. Chem. Soc. 1994, 116, 3657. (b) Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Götz, R.; Keller, P. A.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621. (c) Kelly, T. R.; Xu, W.; Sundaresan, J. Tetrahedron Lett. 1993, 34, 6173. (d) Kelly, T. R.; Kim, M. H. J. Org. Chem. 1992, 57, 1593. (e) Kelly, T. R.; Bridger, G. J.; Zhao, C. J. Am. Chem. Soc. 1990, 112, 8024. (f) Kelly, T. R.; Li, Q.; Bhushan, V. Tetrahedron Lett. 1990, 37, 161.
73. For examples, see: (a) Kelly, T. R.; Bowyer, M. C.; Bhaskar, K. V.; Bebbington, D.; Garcia, A.; Lang, F.; Kim, M. H.; Jette, M. P. J. Am. Chem. Soc. 1994, 116, 3657. (b) Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Götz, R.; Keller, P. A.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621. (c) Kelly, T. R.; Xu, W.; Sundaresan, J. Tetrahedron Lett. 1993, 34, 6173. (d) Kelly, T. R.; Kim, M. H. J. Org. Chem. 1992, 57, 1593. (e) Kelly, T. R.; Bridger, G. J.; Zhao, C. J. Am. Chem. Soc. 1990, 112, 8024. (f) Kelly, T. R.; Li, Q.; Bhushan, V. Tetrahedron Lett. 1990, 37, 161.
74. For examples, see: (a) Kelly, T. R.; Bowyer, M. C.; Bhaskar, K. V.; Bebbington, D.; Garcia, A.; Lang, F.; Kim, M. H.; Jette, M. P. J. Am. Chem. Soc. 1994, 116, 3657. (b) Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Götz, R.; Keller, P. A.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621. (c) Kelly, T. R.; Xu, W.; Sundaresan, J. Tetrahedron Lett. 1993, 34, 6173. (d) Kelly, T. R.; Kim, M. H. J. Org. Chem. 1992, 57, 1593. (e) Kelly, T. R.; Bridger, G. J.; Zhao, C. J. Am. Chem. Soc. 1990, 112, 8024. (f) Kelly, T. R.; Li, Q.; Bhushan, V. Tetrahedron Lett. 1990, 37, 161.
75. For examples, see: (a) Kelly, T. R.; Bowyer, M. C.; Bhaskar, K. V.; Bebbington, D.; Garcia, A.; Lang, F.; Kim, M. H.; Jette, M. P. J. Am. Chem. Soc. 1994, 116, 3657. (b) Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Götz, R.; Keller, P. A.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621. (c) Kelly, T. R.; Xu, W.; Sundaresan, J. Tetrahedron Lett. 1993, 34, 6173. (d) Kelly, T. R.; Kim, M. H. J. Org. Chem. 1992, 57, 1593. (e) Kelly, T. R.; Bridger, G. J.; Zhao, C. J. Am. Chem. Soc. 1990, 112, 8024. (f) Kelly, T. R.; Li, Q.; Bhushan, V. Tetrahedron Lett. 1990, 37, 161.
76. For examples, see: (a) Kelly, T. R.; Bowyer, M. C.; Bhaskar, K. V.; Bebbington, D.; Garcia, A.; Lang, F.; Kim, M. H.; Jette, M. P. J. Am. Chem. Soc. 1994, 116, 3657. (b) Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Götz, R.; Keller, P. A.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621. (c) Kelly, T. R.; Xu, W.; Sundaresan, J. Tetrahedron Lett. 1993, 34, 6173. (d) Kelly, T. R.; Kim, M. H. J. Org. Chem. 1992, 57, 1593. (e) Kelly, T. R.; Bridger, G. J.; Zhao, C. J. Am. Chem. Soc. 1990, 112, 8024. (f) Kelly, T. R.; Li, Q.; Bhushan, V. Tetrahedron Lett. 1990, 37, 161.
77. For examples, see: (a) Kelly, T. R.; Bowyer, M. C.; Bhaskar, K. V.; Bebbington, D.; Garcia, A.; Lang, F.; Kim, M. H.; Jette, M. P. J. Am. Chem. Soc. 1994, 116, 3657. (b) Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Götz, R.; Keller, P. A.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621. (c) Kelly, T. R.; Xu, W.; Sundaresan, J. Tetrahedron Lett. 1993, 34, 6173. (d) Kelly, T. R.; Kim, M. H. J. Org. Chem. 1992, 57, 1593. (e) Kelly, T. R.; Bridger, G. J.; Zhao, C. J. Am. Chem. Soc. 1990, 112, 8024. (f) Kelly, T. R.; Li, Q.; Bhushan, V. Tetrahedron Lett. 1990, 37, 161.
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86. 13C NMR spectrum.
87. 4 409.2127, found 409.2125.
88. 2) cycles (×3), making quantitative measurement difficult. By insertion of a pressure equalizing dropping funnel containing the alkyne solution above the reaction flask containing the Lindlar catalyst solution, it was possible to degas without concommitant hydrogenation. Following degassing, the alkyne solution was quickly dropped into the catalyst solution whereupon hydrogenation commenced.
89. Stannane 25 was observed to undergo facile destannylation on silica gel.