Solvent-free friedel-crafts cyclization with trichloroacetic anhydride

Synthetic Communications

Volumn 39, Issue 15, 2009, Pages 2664-2673

  Andrews, Ben ^a   Bullock, Kae ^b   Condon, Shannon ^b   Corona, John ^b   Davis, Roman ^a,b   Grimes, John ^b   Hazelwood, Andrew ^a   Tabet, Elie ^b  

^a GLAXOSMITHKLINE   (United States)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Benzothiepins; Benzothiopyrans; Benzoxepins; Dibenzothiepins; Dibenzoxepins; Friedel Crafts cyclization; Tetralones

Indexed keywords

ACID ANHYDRIDE; BENZOTHIEPIN DERIVATIVE; BENZOTHIOPYRAN DERIVATIVE; BENZOXEPIN DERIVATIVE; DIBENZOTHIEPIN DERIVATIVE; DIBENZOXEPIN DERIVATIVE; KETONE DERIVATIVE; REAGENT; SOLVENT; TETRALIN DERIVATIVE; TRICHLOROACETIC ANHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; FRIEDEL CRAFTS REACTION; REACTION ANALYSIS;

EID: 67650311857     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802663394     Document Type: Article

References (14)

1. Fillion, E.; Fishlock, D.; Goll, J.; Wilsily, A. Meldrum's acids as acylating agents in the catalytic intramolecular friedel-crafts reaction. J. Org. Chem.2005, 70, 1316.
2. Milionis, J.; Truce, W. Friedel-Crafts cyclization of x-phenylalkanesulfonyl chlorides. J. Am. Chem. Soc. 1952, 74, 974.
3. Basavaiah, D.; Sharada, D.; Veerendhar, A. A facile tandem construction of C-O and C-C bonds: A novel one-pot transformation of Baylis-Hillman adducts into 2-benzoxepines. Tetrahedron Lett. 2004, 45, 3081.
4. Cui, D.; Kawamure, M.; Shimada, S.; Hayashi, T.; Tanaka, M. Synthesis of 1-tetralones by intramolecular Friedel-Crafts reaction of 4-arylbutyric acids using Lewis acid catalysts. Tetrahedron Lett. 2003, 44, 4007.
5. Fuchibe, K.; Ohshima, Y.; Mitomi, K.; Akiyama, T. Hydrodefluorinations by low-valent niobium catalyst. J. Fluorine Chem. 2007, 128, 1158; DeLucia, M. A.; Wolfe, H. E. Refractories to contain fluorinated waste streams. Waste Management 2000, 20, 449.
6. Douglas, G. H.; Walk, C. R.; Smith, H. Totally synthetic steroid hormones, V: (-)-2,3-Dimethoxyestra-1,3,5(10)-trien-17b-ol and some congeners. J. Med. Chem. 1966, 9, 27.
7. Pelter, A.; Ward, R.; Rao, R. An approach to the biomimetic synthesis of aryltetralin lignans. Tetrahedron 1985, 41, 2933.
8. Bindal, R. D.; Durani, S.; Kapil, R. S.; Anand, N. Utility of 4-trimethylsiloxyphenylmagnesium bromide in Grignard reactions. Synthesis 1982, 405.
9. Davies, J. S.; Davies, V. H.; Hassal, C. H. Biosynthesis of phenols, XX: Synthesis of anthraquinones through carbanions of ortho-substituted benzophenones. J. Chem. Soc. C, 1969, 14, 1873.
10. Bartl, V.; Svatek, E.; Protiva, M. Neurotropic and psychotropic agents, LIX: 3-Methoxy-11-(3-dimethylaminopropylidene)-6H,11H-dibenzo(b,e)thiepin and some related compounds. Coll. Czechoslovak Chem. Commun. 1973, 38, 1596.
11. Crenshaw, R. R. ; Jeffries, A. T.; Luke, G. M.; Cheney, L. C.; Bialy, G. Potential antifertility agents, 1: Substituted diaryl derivatives of benzo[b]thiophenes, benzo[b]furans, 1H-2-benzothiapyrans, and 2H-1-benzothiapyrans. J. Med. Chem. 1971, 12, 1185.
12. Freedman, J.; Stewart, K. T. The preparation of 3,4-dihydro-1-benzoxepin- 5(2H)-ones. J. Heterocycl. Chem. 1989, 26, 1547.
13. Dabral, V.; Ila, H.; Anand, N. Potential antifertility agents--Synthesis of 3-(p-hydroxyphenyl)-4-(3-oxocyclopentyl)hexane and 3-(p-hydroxyphenyl)- 4-(3-oxocyclohexyl)hexane and attempted synthesis of 3-(p-hydroxyphenyl)- 4-(2-methyl-3-oxocyclopentyl)hexane and 3-(p-hydroxyphenyl)-4-(2-methyl- 3-oxocyclohexyl)hexane. Indian J. Chem., Sect. B 1979, 18B (2), 152.
14. Venugopal,V.K.;Rao, N.;Rahman,M. F.;Bhalerao, U. T.;Thyagarajan,G.A study of electronic effects involving electron-deficient nitrogen, part IV: Schmidt and Beckmann rearrangements of isoquinolinones and isothiachromanone. Indian J. Chem., Sect. B 1981, 20B (2), 156.