Synthesis of highly condensed heterocycles using radical reactions

Tetrahedron Letters

Volumn 45, Issue 48, 2004, Pages 8909-8912

  Ganguly, A K ^a   Wang, C H ^a   Misiaszek, J ^a   Chan, T M ^b   Pramanik, B N ^b   McPhail, A T ^c  

^a STEVENS INSTITUTE OF TECHNOLOGY   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c DUKE UNIVERSITY   (United States)

Author keywords

Heterocyclic chemistry; Radical reactions

Indexed keywords

HETEROCYCLIC COMPOUND;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RADICAL REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 7444229107     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.181     Document Type: Article

References (7)

1. A.K. Ganguly, C.H. Wang, M. David, P. Bartner, and T.M. Chan Tetrahedron Lett. 43 2002 6865 and references cited therein
2. A.K. Ganguly, C.H. Wang, T.M. Chan, Y.H. Ing, and A.V. Buevich Tetrahedron Lett. 45 2004 883
3. Ganguly, A. K.; Buevich, A. V.; Chan, T. M.; Wang, C. H.; McPhail, A. T. J. Magn. Reson. Chem., submitted for publication
4. NMR and high-resolution mass spectra of all the compounds described in this paper were consistent with the assigned structures. Assignments were further confirmed using HMBC, HSQC and COSY experiments
5. Excepting compounds 23, 24, 26, 28, 29, 30, 32, 33, 34, 35, 36, 37, 41 and 42, which were oil, all the other compounds described in this paper were crystalline. Crystals were obtained from dichloromethane and hexane. The melting points of compounds 13, 14, 18, 19, 20, 25, 31, 38, 39 and 40 were 132-134, 104-106, 120-122, 160-162, 109-111, 80-82, 121-123, 105-107, 60-61 and 72-74°C, respectively. Yields are indicated in parentheses
6. M.L.E.N. da Mata, W.B. Motherwell, and F. Ujjainwalla Tetrahedron Lett. 38 1997 137
7. Crystallographic data (excluding structure factors) for compound 25 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 250067. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EX, UK [e-mail: deposit@ccdc.cam.ac.uk ]