Syntheses of tetrahydrofurobenzofurans and dihydromethanobenzodioxepines from 5-hydroxy-3-methyl-3H-benzofuran-2-one. Rearrangement and ring expansion under reductive conditions on treatment with hydrides

Journal of Organic Chemistry

Volumn 70, Issue 16, 2005, Pages 6171-6176

  Luo, Weiming ^a   Yu, Qian Sheng ^a   Holloway, Harold W ^a   Parrish, Damon ^b   Greig, Nigel H ^a   Brossi, Arnold ^c  

^a NATIONAL INSTITUTE ON AGING   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

^c UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; ENZYMES; FURAN RESINS; PHENOLS;

CYCLIZATION; DIHYDROMETHANOBENZODIOXEPINES; PYRUVIC ACID; TETRAHYDROFUROBENZOFURANS;

SYNTHESIS (CHEMICAL);

1,4 CYCLOHEXANEDIONE; 5 HYDROXY 3 METHOXYCARBONYLMETHYLENE 3 METHYL 3H BENZOFURAN 2 ONE; 5 HYDROXY 3 METHYL 3H BENZOFURAN 2 ONE; 5 HYDROXY 3A METHYL 2,3,3A,8A TETRAHYDROFURO[2,3 B]BENZOFURAN; 7 HYDROXY 5 METHYL 4,5 DIHYDRO 2,5 METHANO 1,3 BENZODIOXEPINE; ACETYLCHOLINESTERASE; BENZOFURAN DERIVATIVE; CARBAMIC ACID DERIVATIVE; CHOLINESTERASE; CYCLOHEXANE DERIVATIVE; OXEPINE DERIVATIVE; PHYSOVENINE; PYRUVIC ACID; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHOLINESTERASE INHIBITION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; EX VIVO STUDY; REDUCTION;

BENZOFURANS; CHOLINESTERASE INHIBITORS; CHOLINESTERASES; HEAT; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXEPINS;

EID: 23044438552     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0503052     Document Type: Article

References (12)

1. Yu, Q. S.; Liu, C.; Brzostowska, M.; Chrisey, L.; Brossi, A.; Greig, N. H.; Atack, J. R.; Soncrant, T. T.; Rapoport, S. I.; Randunz, H. E. Helv. Chim. Acta 1991, 74, 761.
2. Chen, L.; Nielsen, J.; Hedberg, K.; Dunaiskis, A.; Jones, S.; Russo, L.; Johnson, J.; Ives, J.; Liston, D. J. Med. Chem. 1992, 35, 1429.
3. Luo, W.; Yu, Q. S.; Zhan, M.; Parrish, D.; Deschamps, J. R.; Kulkarini, S.; Holloway, H. W.; Alley, G. M.; Lahiri, D. K.; Brossi, A.; Greig, N. H. J. Med. Chem. 2005, 48, 986.
4. (a) Büchi, G.; Foulkes, D. M.; Kurono, M.; Mitchell, G. F. J. Am. Chem. Soc. 1966, 88, 4534.
5. (b) Büchi, G.; Foulkes, D. M.; Kurono, M.; Mitchell, G. F.; Schneider, R. S. J. Am. Chem. Soc. 1967, 89, 6745.
6. (c) Büchi, G.; Weinreb, S. M. J. Am. Chem. Soc. 1971, 93, 746.
7. Civitello, E. R.; Rapoport, H. J. Org. Chem. 1994, 59, 3775.
8. (a) Graybill, T. L.; Pal, K.; McGuire, S. M.; Brobst, S. W.; Townsend, C. A. J. Am. Chem. Soc. 1989, 111, 8306.
9. (b) McGuire, S. M.; Brobst, S. W.; Graybill, T. L.; Pal, K.; Townsend, C. A. J. Am. Chem. Soc. 1989, 111, 8308.
10. (c) Graybill, T. L.; Casillas, E. G.; Pal, K.; Townsend, C. A. J. Am. Chem. Soc. 1999, 121, 7729.
11. Ozaki, Y.; Quan, Z. S.; Watabe, K. J. Heterocycl. Chem. 1999, 51, 727.
12. Chem3D Molecular Modeling and Analysis; CambridgeSoft Corporation, P113-164.