Synthesis of heterocyclic compounds using radical reactions and evidence for the formation of spiro radical intermediates

Tetrahedron Letters

Volumn 45, Issue 4, 2004, Pages 883-886

  Ganguly, A K ^a   Wang, C H ^a   Chan, T M ^b   Ing, Y H ^b   Buevich, A V ^b  

^a STEVENS INSTITUTE OF TECHNOLOGY   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Heterocyclic chemistry; Radical reactions

Indexed keywords

HETEROCYCLIC COMPOUND; RADICAL; SPIRO COMPOUND; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; RADICAL REACTION; SYNTHESIS;

EID: 0347418214     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.204     Document Type: Article

References (6)

1. Ganguly A.K., Wang C.H., David M., Bartner P., Chan T.M. Tetrahedron Lett. 43:2002;6865.
2. Storey J.M.D. Tetrahedron Lett. 41:2000;8173 Beckwith A.L.J., Storey J.M.D. J. Chem. Soc., Chem. Commun. 1995;977.
3. Storey J.M.D. Tetrahedron Lett. 41:2000;8173 Beckwith A.L.J., Storey J.M.D. J. Chem. Soc., Chem. Commun. 1995;977.
4. Bowman W.R., Heanney H., Jordan B. Tetrahedron. 47:1991;10119. and references cited therein.
5. 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 and NOESY experiments.
6. Excepting compound 30 , which was oil, and compounds 22 , 27 , 28 , 29 , 32 , 33 , and 34 , which were white solids, all the other compounds described in this paper were crystalline. Crystals were obtained from dichloromethane and hexane. The melting points of compounds 11 , 12 , 13 , 15 , 16 , 18 , 19 , 20 , 21 , 24 , 25 , 26 , and 31 were 89-91, 65-67, 75-77, 67-69, 79-80, 142-143, 127-128, 148-149, 177-178, 105-107, 64-66, 51-52, and 138-140 °C, respectively. Yields are indicated in parentheses.