The Preparation of 4,5-Dihydro-3-Aryl-Naphth-[1,2-c]- Isoxazoles From Dilithiated 1-Tetralone Oxime and Aromatic Esters

References

• Lang , S. A. Jr. and Lin , Y I . 1984 . “Comprehensive Heterocyclic Chemistry” , Edited by: Potts , K. E. Vol. 6, Part 4B , 61 – 82 . New York : Pergamon Press .
   Google Scholar
• Quilico , A. 1962 . “The Chemistry of Heterocyclic Compounds” , Edited by: Wiley , R. H. 5 – 35 . New York : Interscience Publishers, New York . Several recent synthesis reports
   Google Scholar
• Alberola , A. , Banez , J. M. , Calvo , L. , Rodriguez , M. T. and Sanudo , M. C. 1993 . J. Heterocycl. Chem. , 30 : 467
   Web of Science ®Google Scholar
• Wei , X. , Fang , J. , Hu , Y. and Hu , H. 1992 . Synthesis , : 1205
   Google Scholar
• Moriya , O. , Nakamura , H. , Kageyama , T. and Urata , Y. 1989 . Tetrahedron Lett. , 30 : 3987
   Google Scholar
• Balasundaram , B. and Perumal , P. T. 1990 . Synthetic Communications , 20 : 3161
   Web of Science ®Google Scholar
• 114 – 127 . See ref. 1a.
   Google Scholar
• Wunch , K. H. and Boulton , A. J. 1967 . Adv. Heterocycl. Chem. , 8 : 277
   Google Scholar
• Ogata , M. , Matsumoto , H. and Kano , H. 1969 . Tetrahedron , 52 : 5205
   Google Scholar
• Singeman , G. M. 1975 . J. Heterocycl. Chem. , 12 : 877
   Google Scholar
• Wrobel , Z. and Makosza , M. 1995 . Heterocycl. , 40 : 187
   Google Scholar
• Davis , R. B. and Pizzini , L. C. 1960 . J. Org. Chem. , 25 : 1884
   Web of Science ®Google Scholar
• Johnson , W. S. and Shelberg , W. E. 1945 . J. Am. Chem. Soc. , 67 : 1745
   Web of Science ®Google Scholar
• Suzuka , Y. and Minami , N. Japan Kokkai JP. . 48099161 . Chem. Abstr.197480: 95923.
   Google Scholar
• Sami , M. I. , Gandhi , K. K. and Ray , J. K. 1991 . Org. Prep. Proced. Int. , 23 : 186
   Web of Science ®Google Scholar
• Nitz , T. J. , Volkots , D. L. , Aldous , J. A. and Oglesby , R. C. 1994 . J. Org. Chem. , 59 : 5828
   Web of Science ®Google Scholar
• Barber , G. N. and Olofson , R. A. 1978 . J. Org. Chem. , 43 : 3015
   Web of Science ®Google Scholar
• Basel , Y. and Hassner , A. 1997 . Synthesis , : 309
   Google Scholar
• Moriya , O. , Takenaka , H. , Iyoda , M. , Urata , Y. and Endo , T. 1999 . J. Chem. Soc., Perkin Trans 1 , : 413
   Google Scholar
• Sakamoto , T. , Uchiyama , D. , Kondo , Y. and Yamanaka , H. 1993 . Chem. Pharm. Bull. , 41 : 478
   Google Scholar
• Beam , C. F. , Dyer , M. C. D. , Schwarz , R. A. and Hauser , C. R. 1970 . J. Org. Chem. , 35 : 1806
   Web of Science ®Google Scholar
• Beam , C. F. , Foote , R. S. and Hauser , C. R. 1972 . J. Heterocycl. Chem. , 9 : 183
   Web of Science ®Google Scholar
• Sandifer , R. M. , Dasher , L. W. , Hollinger , W. M. , Thomas , C. W. , Reames , D. C. , Beam , C. F. , Foote , R. S. and Hauser , C. R. 1975 . J. Heterocycl. Chem. , 72 : 1159
   Google Scholar
• Perkins , M. , Beam , C. F. , Dyer , M. C. D. and Hauser , C. R. 1975 . Org. Synth. , 55 : 39
   Google Scholar
• Sandifer , R. M. , Shaffer , L. M. , Hollinger , W. M. , Reames , D. C. and Beam , C. F. 1976 . J. Heterocycl. Chem. , 13 : 607
   Web of Science ®Google Scholar
• Beam , C. F. , Shealy , K. D. , Harris , C. E. , Shealy , N. L. , Dasher , L. W. , Hollinger , W. M. , Sandifer , R. M. and Reames , D. C. 1976 . J. Pharm. Sci. , 65 : 1408
   PubMedGoogle Scholar
• Fulmer , T. D. , Dasher , L. P. , Bobb , B. L. , Wilson , J. D. , Sides , K. L. and Beam , C. F. 1980 . J. Heterocycl. Chem. , 17 : 799
   Web of Science ®Google Scholar
• Livingston , M. J. , Chick , M. F. , Shealy , E. O. , Park , D. J. , Fulmer , T. D. and Beam , C. F. 1982 . J. Heterocycl. Chem. , 19 : 215
   Web of Science ®Google Scholar
• Huff , A. M. , Hall , H. L. , Smith , M. J. , O'Grady , S. A. , Waters , F. C. , Fengl , R. W. , Welch , J. A. and Beam , C. F. 1985 . J. Heterocycl. Chem. , 22 : 501
   Web of Science ®Google Scholar
• Davis , S. E. , Church , A. C. , Scott , A. S. , Throckmorton , H. L. , Studer-Martinez , S. L. and Beam , C. F. 1997 . J. Organometal. Chem. , 533 : 125
   Web of Science ®Google Scholar
• Williams , A. J. , Angel , A. J. , French , K. L. , Hurst , D. R. , Beckman , D. D. and Beam , C. F. 1977 . Synthetic Communications , 29 : 199
   Google Scholar
• Williams , A. R. , Finefrock , A. E. , Townsend , J. D. , Angel , A. J. , Hurst , D. R. , Rampey , M. E. , Halkyard , C. E. , Studer-Martinez , S. L. and Beam , C. F. 1998 . The Chemist , 75 : 7
   Google Scholar
• Hoskin , D. H. and Olofson , R. A. 1982 . J. Org. Chem. , 47 : 5222
   Web of Science ®Google Scholar
• Fos , E. , Borras , L. , Gasull , M. , Mauleon , D. and Carganico , G. 1992 . J. Heterocycl. Chem. , 29 : 203
   Web of Science ®Google Scholar
• Shriner , R. L. , Hermann , C. K. F. , Morrill , T. C. , Curtin , D. Y. and Fuson , R. C. , eds. 1997 . “ The preparation of the oxime from 1-tetralone involved a minor modification of a well documented procedure where 20 g of hydroxylamine hydrochloride was dissolved in 120 mL of water followed by the addition of 80 mL of 10% NaOH solution. The solution was placed in a flask or beaker and heated on a stir plate while 20 g of 1-tetralone dissolved in 30--40 mL of ethanol was added along with enough extra ethanol to affect the solution. The solution was heated just enough to slowly boil off solvents [fume hood], and finally an olly layer/phase appeared. The mixture was refrigerated, and crystallization occurred immediately. After filtration, the solid was recrystallized from ethanol, and it was dry enough after filtration for immediate use [15--20 min.], although use of a vacuum desiccator is recommended, [80--90% yield after recrystallization from ethanol] ” . In “The Systematic Identification of Organic Compounds”, , seventh edition , 323 New York : John Wiley and Sons, Inc., New York .
   Google Scholar
• Melting points were obtained with a Mel-Temp II melting point apparatus in open capillary tubes and are uncorrected. ,
   Google Scholar
• Shriner , R. L. , Hermann , C. K. F. , Morrill , T. C. , Curtin , D. Y. and Fuson , R. C. , eds. 1997 . Combustion analyses for C, H and N , 323 Whitehouse, NJ : Quantitative Technologies, Inc. . P.O. Box 470, Salem Industrial Park, Bldg. 5, 08888.
   Google Scholar
• NMR Data; compd. no., (solvent), [300 MHz] 1H NMR, 13C NMR, δ ppm: 1. 1H NMR (DMSO-d6), 3.02 (s, 4H, CH2CH2), 7.26--7.53, 7.77--7.80, and 8.00--8.03 (m, 9H, ArH); 13C NMR (DMSO-d6), 18.4, 28.2, 110.8, 123.6, 125.0, 125.9, 127.1, 127.4, 128.3, 129.1, 129.7, 130.2, 137.8, 159.1, and 161.5. 2. 1H NMR (DMSO-d6), 3.14 (s, 4H, CH2CH2), 4.00 (s, 3H, ArOCH3), and 7.27--8.03 (m, 8H, ArH); 13C NMR (DMSO-d6), 18.3, 28.2, 55.3, 109.2, 114.5, 120.1, 123.6, 125.1, 127.0, 127.4, 128.8, 130.1, 137.7, 158.9, 160.1, and 161.7. 3. 1H NMR (CDCl3), 2.96 (s, 4H, CH2CH2) 3.81 (s, 6H, OCH3), 6.88--8.03 (m, 7H, ArH); 13C NMR (CDCl3), 19.2, 28.8, 55.3, 101.3, 104.1, 110.6, 124.1, 125.6, 126.9, 128.3, 129.6, 129.8, 137.3, 159.4, 160.7, and 161.8. 4. 1H NMR (CDCl3), 3.00 (s, 4H, CH2CH2), 3.93 (s, 3H, OCH3), 3.97 (s, 3H, OCH3), 6.94 (s, 1H, ArH), 7.26--7.39 and 7.98--8.01 (m, 6H, ArH); 13C NMR (CDCl3), 19.6, 29.4, 56.30, 56.36, 109.4, 109.6, 111.4, 119.5, 121.6, 124.6, 126.2, 127.4, 128.8, 130.2, 137.7, 149.4, 150.3, 159.9, and 162.5. 5. 1H NMR (CDCl3), 3.02 (s, 4H, CH2CH2), 3.91 (s, 3H, ArOCH3), 3.94 (s, 6H, ArOCH3), 6.87 (s, 2H, ArH), 6.99, 7.27--7.38 and 7.98--8.01 (m, 4H, ArH); 13C NMR (CDCl3) 19.5, 29.2, 56.5, 61.2, 103.7, 110.2, 123.9, 124.5, 126.0, 127.3, 128.6, 130.1, 137.5, 139.3, 153.6, 159.8, and 162.2. 6. 1H NMR (CDCl3), 2.35 (s, 3H, ArCH3) 3.02 (s, 4H, CH2CH2), 6.87 (s, 2H, ArH), 7.27--7.36 and 7.95--7.98 (m, 4H, ArH); 13C NMR (CDCl3), 19.5, 21.6, 29.3, 110.4, 124.1, 124.5, 126.1, 127.2, 128.3, 128.6, 130.0, 131.3, 137.7, 138.6, 159.7, and 162.7. 7. 1H NMR (CDCl3), 1.35 (s, 9H, C(CH3 3), 3.00 (s, 4H, CH3CH3), 7.24--7.38, 7.48--7.52, 7.65--7.74, and 7.74--8.01 (m, 8H, ArH); 13C NMR (CDCl3), 19.4, 29.3, 31.4, 35.1, 110.2, 124.5, 125.7, 125.9, 126.10, 126.14, 127.2, 128.7, 130.1, 137.7, 152.8, 159.8, and 162.6. 8. 1H NMR (CDCl3), 2.37 (s, 6H, ArCH3), 2.99 (s, 4H, CH2CH2), 7.05 (s, 1H, ArH), 7.23--7.37 and 7.97--8.00 (m, 6H, ArH); 13C NMR (CDCl3), 19.3, 21.4, 29.1, 110.2, 123.8, 124.2, 125.9, 127.0, 128.1, 128.4, 129.8, 131.0, 137.4, 138.3, 159.5, and 162.5. 9. 1H NMR (CDCl3), 2.89 (s, 4H, CH2CH2) 7.12--7.32, 7.51--7.62, (m, 7H, ArH), and 7.85 (d, 1H, ArH); 13CNMR (CDCl3), 19.1, 28.7, 111.1, 124.0, 124.2, 125.4, 125.8, 127.0, 128.3, 129.1, 129.6, 129.89, 129.93, 134.6, 137.1, 159.5, and 160.5. 10. 1H NMR (DMSO-d6;), 3.00 (s, 4H, CH2CH2), 7.35--7.47, 7.61--7.63, and 7.79--7.87 (m, 8H, ArH); 13C NMR (DMSOA), 18.3, 28.0, 111.3, 123.7, 124.9, 126.3, 127.2, 127.7, 128.9, 129.3, 130.4, 134.5, 137.8, 159.3, and 160.6. 11. 1H NMR (CDCl3), 3.00 (s, 4H, CH2CH2), 7.25--7.35, 7.58--7.65, and 7.65--7.99 (m, 8H, ArH); 13C NMR (CDCl3), 19.5, 29.2, 111.1, 123.9, 124.6, 125.8, 127.3, 127.4, 127.7, 128.7, 130.3, 132.3, 137.5, 159.9, and 161.3. 12. 1H NMR (CDCl3), 2.98 (s, 4H, CH2CH2), 7.12--7.38, 7.70--7.76, and 7.96--7.99 (m, 8H, ArH); 13C NMR (CDCl3), 19.4, 29.2, 110.3, 116.0, 116.3, 124.5, 124.7, 124.8, 125.9, 127.3, 128.2, 128.3, 128.7, 130.2, 137.5, 159.8, 161.46, 161.52, and 164.8; 19F NMR (CDC13), --110.5; see also: ref. 13 a, b. 13. 1H NMR (CDCl3/DMSOd6), 3.17 (s, 4H, CH2CH2), 6.69--6.81, 7.08--7.28, and 7.60--7.63 (m, 8H, ArH) and 10.22 (s, 1H, ArOH); 13C NMR (CDCl3/DMSO-d6), 19.0, 28.4, 112.0, 114.8, 116.3, 119.2, 123.6, 125.4, 127.0, 128.8, 129.3, 130.0, 131.3, 138.1, 154.7, 158.7, and 161.2. 14. 1H NMR (CDCl3/DMSO-d6), 2.97 (s, 4H, CH2CH2), 6.87--6.91, 7.18--7.44, and 7.82--7.84 (m, 8H, ArH), and 9.85 (s, 1H, ArOH); 13CNMR (CDCl3/DMSO-d6), 18.5, 28.2, 110.6, 112.3, 116.6, 116.9, 123.6, 125.0, 127.1, 128.5, 128.8, 130.2, 130.3, 137.8, 157.7, 159.0, and 161.6. 15. 1H NMR (DMSO-d6), 2.98 (s, 4H, CH2CH2), 6.97 and 7.66 (d, d, 4H, ArH), 7.38--7.44, 7.84--7.87 (m, 4H, ArH), and 10.11 (s, 1H, ArOH); 13C NMR (DMSO-d6), 18.4, 28.3, 108.5, 115.9, 118.6, 123.6, 125.2, 127.0, 127.6, 128.8, 130.0, 137.7, 158.7, 158.9, and 162.1. 16. 1H NMR (DMSO-d6), 2.93 (s, 4H, CH2, 5.71 (s, 1H, NH2), 6.73 and 7.48 (d, d, 4H, ArH), 7.31--7.50 (m, 3H, ArH), and 7.81 (d, 1H, ArH); 13CNMR (DMSO-d6) 18.5, 28.4, 107.0, 113.7, 114.9, 123.5, 125.5, 126.9, 127.1, 128.7, 129.9, 137.7, 150.3, 158.7, and 162.9. 17. 1H NMR (CDCl), 2.97 (s, 6H, ArN(CH3 2), 3.00 (s [minor splitting], 4H CH2CH2), 6.73--6.78, 7.24--7.34, and 7.62--7.99 (m, 8H, ArH); 13C NMR (CDCl3), 19.4, 29.4, 40.4, 107.9, 112.0, 116.4, 124.4, 126.4, 127.1, 127.4, 128.6, 129.8, 137.7, 150.9, 159.6, and 162.3.
   Google Scholar
• Infrared spectra (paraffin oil mulls) were obtained with a Nicolet Impact 410 FT-IR. ,
   Google Scholar
• Silverstein , R. M. and Webster , F. X. , eds. 1998 . “ IR spectra for ethyl 4-aminobenzoate displayed absorptions at 3324, 3213 and 3640, cm-1 ” . In “Spectrometric Identification of Organic Compounds” , sixth edition , 102 New York : John Wiley and Sons, Inc., New York .
   Google Scholar
• Proton and ¹³C NMR spectra were obtained with a Varian Associates Mercury Oxford 300 MHz, nuclear magnetic resonance spectrometer, and chemical shifts are recorded in δ ppm downfield from an internal tetramethylsilane (TMS) standard. ,
   Google Scholar
• A ¹³C NMR spectra for ethyl 4-fluorobenzoate also displayed ¹³C-¹⁹F coupling with eleven lines for the molecule containing seven distinct carbon atoms. ,
   Google Scholar
• A ¹⁹F NMR spectra for ethyl 4-fluorobenzoate displayed an absorption at δ - 106.7 ppm. ,
   Google Scholar
• When 1-indanone oxime was dilithiated with excess LDA and condensed with aromatic esters, the attempted cyclization resulted in a C-acylated product or sometimes an incompletely characterized second product and not the expected indeno-isoxazole. ,
   Google Scholar
• Rampey , M. E. , Hurst , D. R. , Sood , A. , Studer-Martinez , S. L. and Beam , C. F. 1999 . The extension of this methodology to non commercially available 8-hydroxy-1-tetralones and related compounds is currently under investigation . Synthetic Communications , 29 : 487
   Google Scholar
• Studer-Martinez , S. L. , Rampey , M. E. , Halkyard , C. E. , Williams , A. R. , Angel , A. J. , Hurst , D. R. , Townsend , J. D. , Finefrock , A. E. and Beam , C. F. 1999 . Photochem. and Photobiol. , 70 : 176
   Google Scholar
• See also: ref. 7f.
   Google Scholar
• The condensation time differs due to the pendant group on the phenyl ring. The usual condensation time is approximately 1 hr for esters resulting in compounds such as 1, and 6--12; electron donating groups, such as methoxy, whether or not in a resonance position relative to the ester carboxyl group for products 2--5 are generally condensed longer, 1.25 - 1.5 hr; and esters with strong electron donating groups such as anilino or phenoxide for products 13--17 are condensed for an even longer period of time, 2 - 2.5 hr.
   Google Scholar