Azaphilone α-Bromoacetates (AzαBs): Fluorescent linchpin reagents for the inter- and intramolecular cross-linkage of primary amines to thiols

Letters in Organic Chemistry

Volumn 6, Issue 5, 2009, Pages 367-371

  Chruma, Jason J ^a   Moon, Sung Ju ^a   Sanford Jr , William E ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

Azaphilones; Bioconjugation; Cross linkage; Fluorescent; Orthogonal reactivity

Indexed keywords

EID: 69549126386     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017809788681428     Document Type: Article

References (21)

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16. 3, 125 MHz) δ 191.5, 168.2, 157.2, 153.8, 142.8, 131.6, 130.1, 129.1, 125.6, 115.2, 107.8, 107.2, 85.8, 60.4, 24.8, 22.5, 22.5, 21.0, 14.2.
17. Porco reported that 3 equiv of AcOH in THF was necessary for high yielding γ-pyridone formation in a related system; Zhu, J.; Gemain, A. R.; Porco, J. A., Jr. Angew. Chem. Int. Ed. Engl., 2004, 43, 1239.
18. 3, 75 MHz) δ 194.4, 190.3, 170.6, 166.2, 149.3, 142.8, 134.3, 129.6, 128.9, 126.1, 116.7, 115.1, 99.4, 85.8, 56.7, 31.7, 31.5, 29.0, 28.8, 28.3, 25.4, 23.2, 22.5, 14.0.
19. 3, though 4 hours are required for complete conversion of 4 to 5a.
20. 3, 75 MHz) δ 194.8, 191.1, 169.5, 148.9, 148.8, 142.7, 134.5, 129.5, 128.8, 126.0, 116.5, 114.9, 99.5, 85.1, 56.5, 32.5, 32.1, 31.9, 31.6, 29.6, 29.5, 29.3, 29.2, 29.0, 28.8, 28.3, 23.1, 22.6, 22.5, 14.1, 14.0.
21. 6- acetone, 125 MHz) δ 197.9, 191.6, 172.2, 172.1, 171.0, 168.0, 157.9, 152.2, 150.7, 145.1, 141.3, 141.1, 138.9, 130.2, 129.6, 129.5, 129.4, 129.2, 128.4, 127.6, 124.2, 121.7, 116.8, 116.5, 100.1, 87.5, 67.9, 67.9, 56.2, 55.9, 55.9, 45.0, 44.9, 44.2, 36.5, 34.5, 33.5, 33.4, 29.5, 24.4, 24.2, 15.3.