A convenient synthesis of ortho-ortho disubstituted biphenyls containing an eight-membered lactam ring using radical chemistry

Tetrahedron Letters

Volumn 50, Issue 17, 2009, Pages 1879-1881

  Wang, C H ^a   Alluri, S ^a   Ganguly, A K ^a  

^a Stevens Institute of Technology   (United States)

Author keywords

Ortho ortho disubstituted biphenyls; Radical reaction

Indexed keywords

ANTIMITOTIC AGENT; BIPHENYL DERIVATIVE; N2 [2 (3,5 DIFLUOROPHENYL) 2 HYDROXYACETYL] N1 (6,7 DIHYDRO 5 METHYL 6 OXO 5H DIBENZ[B,D]AZEPIN 7 YL)ALANINAMIDE; RHAZINILAM; STEGANACIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG MECHANISM; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; METHYLATION;

EID: 61749103011     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.031     Document Type: Article

References (12)

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9. The purity of the compounds was established using various chromatographic techniques. NMR and high resolution mass spectra of all the compounds described in this letter were consistent with the assigned structures. Assignments were further confirmed using 2D NMR and NOE experiments.
10. Excepting compounds 10, 11, 16, 20, 24, and 25, all the other compounds described in this Letter were crystalline. Crystals were obtained from dichloro-methane and hexane. The melting points of compounds 4, 9, 15, 17, 18, 19, 21, 22, and 23 were 163-165, 195-197, 180-182, 160-162, 187-189, 179-181, 191-193, 156-158, and 101-103 °C, respectively. Yields are indicated in parentheses.
11. 2 group at δ 2.7-2.5 (m, 2H, H-c), and a CH group at δ 4.4 (td, J = 9.3 Hz, J = 7.1 Hz, 1H, H-d). The amine proton H-e appeared at δ 3.9 (d, J = 9.3 Hz, 1H) and the amide hydrogen H-f showed a singlet at δ 8.0.
12. 13CNMR spectrum, the two quaternary carbons appeared at δ 60.1 (C-d) and δ 78.0 (C-e).