The Preparation of Substituted 1(2H)-Isoquinolinones from Polylithiated 2-(2-Methylphenyl)Hydrazinecarboxylic Acid Esters

REFERENCES

• Vaulx , R. L. , Puterbaugh , W. H. and Hauser , C. R. 1964 . J. Org. Chem. , 29 : 3514
   Google Scholar
• Mao , C. -L. , Barnish , IT. and Hauser , C. R. 1969 . J. Heterocyclic Chem. , 6 : 83
   Google Scholar
• Watanabe , H. , Mao , C. -L. and Hauser , C. R. 1969 . J. Org. Chem. , 34 : 1786
   Google Scholar
• Mao , C. -L. and Hauser , C. R. 1970 . J. Org. Chem. , 35 : 3704
   Google Scholar
• Wasserman , H. H. and Lipshutz , K. H. 1975 . Tetrahedron Lett. , : 1731
   Google Scholar
• Mali , R. S. , Kuklarni , B. K. and Shankaran , K. 1982 . Synthesis , : 329
   Google Scholar
• Bailey , D. M. and De Garzia , C. G. 1970 . J. Org. Chem. , 35 : 4088
   Google Scholar
• Bailey , D. M. and DeGarzia . 1970 . Tetrahedron Lett. , 9 : 633
   Google Scholar
• Beam , C. F. , Park , C. A. , Reames , D. C. , Miller , S. J.A. and Hauser , C. R. 1978 . J. Chem. and Eng. Data. , 23 : 183
   Google Scholar
• Pelletier , S. W. 1970 . Chemistry of Alkaloids , 77 New York, New York : Van Nostrand Reinhold Co. .
   Google Scholar
• Shamma , M. and Mionot , J. L. 1978 . Isoquinoline Alkaloid Research , 51 New York, New York : Plenum Press .
   Google Scholar
• Iida , H. , Kawano , K. , Kikuchi , T. and Yoshimizu . 1976 . Yakuggaka Zasshi , 96 : 176
   PubMedGoogle Scholar
• Girling , I. R. and Widdowson , D. A. 1988 . J. Chem. Soc., Perkin Trans. , 1 : 1317
   Google Scholar
• VanderGoot. , H. and Nauta , W. Th. 1971 . Acta Pharm. Suecica , 8 : 373
   PubMedGoogle Scholar
• Izumi , T. and Marishita , N. 1994 . J. Heterocycl. Chem , 31 : 145
   Web of Science ®Google Scholar
• Cobas , A. , Guitian , E. and Castedo , L. 1993 . J. Org. Chem. , 58 : 3113
   Google Scholar
• Couture , A. , Cornet , H. and Grandclaudon , P. 1992 . J. Organometal. Chem. , 440 : 7
   Google Scholar
• Couture , A. and Grandclaudon , P. 1992 . Tetrahedron , 49 : 3857
   Google Scholar
• Stanoeva , E. , Haimova , M. and Ognyanov , V. 1984 . Liebigs Ann., Chem. , : 389
   Google Scholar
• Ueno , S. , Sugihara , K. , Hirayama , H. and Ichino , M. Japan Kokai . 76,122,075 . 1976 . 2-Acylamino-3-phenyl-1(2H)-isoquinolinones: Chem. Abstr., 1977, 87: 5822a
   Google Scholar
• Huisgen , R. and Rauenbusch , E. 1961 . Ann. , 641 : 51 2-Amino-1(2H)-isoquinolinones:
   Google Scholar
• Boyers , J. T. and Glover , E. E. 1977 . J. Chem. Soc., Perkin Trans. , 1 : 1960
   Google Scholar
• Datta , D. and Usgaonkae . 1981 . Indian J. Chem. , 20B : 376
   Google Scholar
• Gurevich , A. I. , Kolasov , M. N. , Omelchenko , V. N. , Onoprienko , V. V. and Petrenko , G. I. 1975 . Bioorg. Khim. , 1 : 166
   Google Scholar
• Legrand , L. and Lozac'h . 1970 . Bull. Soc. Chem. Fr. , : 2240
   Google Scholar
• Grekov , A. P. and Veselov , V. A. 1971 . Zh. Org. Khim. , 7 : 323 Only the ethyl 2-(3-methylphenyl)hydrazinecarboxylate and 2-(4-methylphenyl)hydrazinecrboxylate isomers have been reported. See: Chem. Abstr. 1971, 75: 48108s
   Google Scholar
• (a) We found Schotten-Baumann condensation procedures of aromatic carboxylic acid chlorides too general. In order to avoid excess diacylation and still be able to make the entry compound expediently, we used a procedure that gave the desired entry compounds in 50 - 70% yield.
   Google Scholar
• Carpino , L. A. , Terry , P. H. and Crowley , P. J. 1961 . J. Org. Chem. , 26 : 4336 See also:
   Web of Science ®Google 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
• 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
• Duncan , D. C. , Trumbo , T. A. , Almquist , CD. , Lentz , T. A. and Beam , C. F. 1987 . J. Heterocycl. Chem. , 24 : 555
   Web of Science ®Google Scholar
• We noted the following resonance absortions for these products, which were not starting materials: 1H nmr (CDCl3), δ 2.47 and 2.60 ppm (ArCH3). The spectra indicated that metalation of the ortho methyl hydrogens had not occurred.
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• Infrared spectra were obtained from a Mattson Polaris FT-Infrared Spectrometer. 1H nmr were obtained from a Varian Associates, EM-360L Nuclear Magnetic Resonance Spectrometer, and chemical shifts are reported in δ ppm downfield from an internal tetramethylsilane (TMS) standard. [Compound No. from Table, ir (paraffin oil), cm−1; nmr (solvent);] Compd. 1; ir, 3379 (OH), 3313 (NH), 1721 (C=O), and 1646 (N-C=O); nmr (DMSO-d6) δ 1.17 (t, CH3), 4.11 (q, -OCH2-), 6.68 (s, C4-H), 6.77 - 7.88 and 8.20 - 8.43 (m, ArH), and 10.30 (s, broad, ArOH). Compd. 2; ir, 3426 (OH), 3239 (NH), 1722 (C=O), and 1653 (N-C=O); nmr (DMSO-d6) δ 3.68 (s, OCH3), 6.63 (s, C4-H), and 6.78 - 7.88 and 8.13 - 8.45 (m, ArH). Compd. 3; ir, 3354 (OH), 3212 (NH), 1745 (C=O), and 1638 (Ar and N-C=O); nmr (DMSO-d6/ CDCl3), δ 1.40 (s, -OC(CH3)3), 6.48 (s, C4-H), 6.70–8.55 (m, ArH). Compd. 4; ir, 3179 (NH), 1749 (C=O), 1648 (Ar and N-C=O); nmr (CDCl3) δ 1.10 (t, CH3-), 2.38 (s, ArCH3), 4.10 (q, -OCH2-), 6.50 (s, C4-H), 7.13 - 7.73 and 8.30 - 8.53 (m, ArH). Compd. 5; ir, 3250 (NH), 1720 (C=O), and 1681 (Ar and N-C=O); nmr (CDC13) δ 1.15 (t, CH3-), 1.33 (s, Ar-C(CH3)3), 4.16 (q, -OCH2-), 6.52 (s, C4-H), and 7.25 - 7.77 and 8.33 - 8.58 (m, ArH). Compd. 6; ir, 3180 (NH), 1746 (C=O), 1652 (Ar and N-C=O); nmr (CDCl3) δ 1.38 (s, -OC(CH3)3), 6.53 (s, C4-H), and 7.22 - 7.88 and 8.35 - 8.65 (m, ArH). Compd. 7; ir, 3265 (NH), 1726 (C=O), and 1687 (Ar and N-C=O); nmr (CDCl3) δ 1.37 (s, ArC(CH3)3), 6.55 (s, C4-H), 3.72 (s, OCH3), and 7.28 - 7.88 and 8.33 - 8.63 (m, ArH). Compd. 8; ir, 3174 (NH), 1747 (C=O), and 1648 (Ar and N-C=O); nmr (CDCl3) δ 1.42 (s, -OC(CH3)3), 6.52 (s, C4-H), and 7.23 - 7.78 and 8.40 - 8.63 (m, ArH). Compd. 9; ir, 3218 (NH), 1744 (C=O), and 1668 (Ar and N-C=O); nmr (CDCl3) δ 1.13 (t, CH3-), 4.14 (q, -OCH2-), 6.52 (s, C4-H), and 7.33 - 7.87 and 8.33 - 8.55 (m ArH). Compd. 10; ir, 3171 (NH), 1742 (C=O), 1643 (Ar and N-C=O); nmr (DMSO-d6) δ 1.35 (s, -OC(CH3)3), 3.80 (s, -OCH3), 6.63 (s, C4-H), and 6.90 - 7.88 and 8.13 - 8.45 (m, ArH). Compd. 11; ir, 3176 (NH), 1749 (C=O), 1653 (Ar and N-C=O); nmr (CDCl3) δ 1.20 (t, CH3-), 4.16 (q, -OCH2-), 3.88 and 3.92 (s, ArOCH3), 6.53 (s, C4-H), and 7.43 - 7.87 and 8.30 - 8.63 (m, ArH). Compd. 12; ir, 3288 (NH), 1745 (C=O), and 1670 (N-C=O) cm−1; nmr (CDCl3) δ 1.42 (s, -OC(CH3)3), 3.88 and 3.90 (s, ArOCH3), 6.53 (s, C4-H), and 6.77 - 7.80 and 8.37 - 8.57 (m, ArH). Compd. 13; ir, 3178 (NH), 1726 (C=O), and 1681 (Ar and N-C=O); nmr (CDC13) δ 3.70 (s, OCH3), 6.55 (s-br, CH=C, enol), and 7.17 - 7.77 and 8.37 - 8.57 (m, ArH). Compd. 14; ir, 3242 broad (NH), 1737 (C=O-O), and 1662 cm−1 (C=O-N and Ar); nmr (DMSO-d6) δ 2.28 (s, ArCH3), 3.65 (s, -OCH3), and 7.18 - 7.55 (m, ArH). Compd. 15; ir, 3321 and 3233 (NH), 1732 (C=O-O), and 1663 (C=O-N and Ar); nmr (CDCl3/DMSO-d6) δ 1.25 (t, -CH3), 2.42 (s, ArCH3), 4.16 (q, -OCH2-), and 7.13 - 7.68 (m, ArH). Compd 16; ir, 3330 and 3244 (NH), 1722 (C=O-O), and 1660 (C=O-N and Ar); nmr (CDCl3) δ 1.43 (s, -OC(CH3)3), 2.43 (s, ArH) and 7.12 - 7.68 (m, ArH).
   Google Scholar
• Microanalysis for C, H, and N were performed by Quantitative Technologies, Inc., P.O. Box 470, Salem Industrial Park, Bldg. 5, Whitehouse, NJ 08888 and Robertsons Laboratory, 8 Samson Avenue, Madison, NJ 07940. [Compd. No. from Table] Calcd. for 1: C, 66.66; H, 4.97; N, 8.64. Found: C, 66.90; H, 5.13; N, 8.37. Calcd. for 2: C, 65.80; H, 4.55; N, 9.03. Found: C, 65.74; H, 4.80; N, 8.74. Calcd. for 3: C, 68.17; H, 5.72; N, 7.95. Found: C, 68.16; H, 5.79; N, 7.96 Calcd. for 4: C, 70.79; H, 5.63; N, 8.69. Found: C, 70.49; H, 5.65; N, 8.65. Calcd. for 5: C, 72.51; H, 6.64; N, 7.69. Found: C, 72.54; H, 6.50; N, 7.69. Calcd. for 6: C, 71.41; H, 5.99; N, 8.33. Found: C, 71.40; H, 6.05; H, 8.25. Calcd. for 7: C, 71.98; H, 6.33; N, 7.99. Found: C, 72.04; H, 6.47; N, 7.88. Calcd. for 8: C, 64.78; H, 5.16; N, 7.55. Found: C, 664.93; H, 5.13; N, 7.58. Calcd. for 9: C, 63.07; H, 4.41; N, 8.17. Found: C, 63.15; H, 4.55; N, 8.07. Calcd. for 10: C, 68.84; H, 6.05; N, 7.64. Found: C, 68.88; H, 6.09; N, 7.56. Calcd. for 11: C, 63.31; H, 5.57; N, 7.03. Found: C, 63.22; H, 5.74; N, 6.88. Calcd. for 12: C, 64.78; H, 6.14; N, 6.57. Found: C, 64.69; H, 6.21; N, 6.66. Calcd. for 13: C, 65.38; H, 5.16; N, 8.96. Found: C, 65.34; H, 5.28; N, 8.85. Calcd. for 14: C, 57.69; H, 5.81; N, 13.45. Found: C, 57.77; H, 5.86; N, 13.49. Calcd. for 15: C, 59.45; H, 6.35; N, 12.60. Found: C, 59.38; H, 6.44; N, 12.46. Calcd. for 16: C, 62.38; H, 7.25; N, 11.19. Found: C, 62.43; H, 6.99; N, 11.19.
   Google Scholar
• Brown , J. , Sides , K. L. , Fulmer , T. D. and Beam , C. F. 1979 . J. Heterocycl. Chem. , 16 : 1669
   Google Scholar
• Mack , H. M. , Davis , E. A. , Kadkhodayan , B. , Taylor , R. A. , Duncan , D. C. and Beam , C. F. 1987 . J. Heterocycl. Chem. , 24 : 1733
   Google Scholar
• There are numerous reports concerning the preparation of 2,3-benzodiazepin-1-ones, and in each case the double bond is between N-3 and C-4, and not between C-4 and C-5. The latter location of the double bond would be in the 2,3-benzodiazepin-1-ones, if formed during the cyclization, prior to rearrangement to the 1(2H)-isoquinolinone
   Google Scholar
• Ames , D. A. and Dodds . 1972 . J. Chem. Soc., Perkin Trans. , 1 : 705
   Google Scholar
• Wolbling , H. 1905 . Ber. , 38 : 3846
   Google Scholar
• Wolbling , H. 1905 . Ber. , : 2845
   Google Scholar
• Flammang , M. and Hebd , C. R. 1978 . Seances Acad. Sci. Ser. C , 286 : 671 Chem. Abstr., 1978, 89: 146878b
   Google Scholar
• Flammang , M. and Wermuth , C. G. 1977 . Eur. J. Med. Chem.-Chim. Ther. , 12 : 121
   Google Scholar
• Flammang , M. and Wermuth , C. G. 1980 . CJl. Hebd. Seances Acad. Sci. Ser. C , 290 : 361 Chem. Abstr., 1980, 93, 203556d
   Google Scholar
• Rose , A. and Buu-Hoi , N. P. 1968 . J. Chem. Soc. , C : 2205
   Google Scholar
• Vorozhtov , N. N. and Petuchkova , A. T. 1957 . J. Gen Chem. USSR (Engl. Trans.) , 27 : 2342
   Google Scholar
• Somei , M. , Karasawa , Y. , Shoda , T. and Kaneko , C. 1981 . Chem. Pharm. Bull, Japan. , 29 : 249
   Google Scholar
• Grogan , F. , O'Brian , A. E. , Philbin , E. M. , O'Conner , N. S. , Tommoney , R. F. and Wheeler , T. S. 1958 . Tetrahedron , 3 : 140
   Google Scholar
• Legrand , L. and Lozac'h , N. 1970 . Bull. Soc. Chim. Fr. , : 2237 and 2240
   Google Scholar
• Initially 95% ethanol was used. If crystals did not form in several hours or overnight (refrigerator), a few drops of water or a few ice crystals were added.
   Google Scholar
• A 1.6 M solution in hexanes was obtained from Aldrich Chemical Co. This material is satisfactory enough to effect metalation and dilute enough to permit expedient and safe handling.
   Google Scholar