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84889526297
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(Monsanto Co.). U.S. Patent 4097260, 1978
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D'Amico, J. J. (Monsanto Co.). U.S. Patent 4097260, 1978.
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D'Amico, J.J.1
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2
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Thomson, K. S.; Hertel, R.; Mueller, S.; Tavares, J. E. Planta 1973, 109, 337.
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Thomson, K.S.1
Hertel, R.2
Mueller, S.3
Tavares, J.E.4
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(a) Bures, M. G.; Black-Schaefer, C.; Gardner, G. J. Comput.-Aided Mol. Des. 1991, 5, 323.
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Bures, M.G.1
Black-Schaefer, C.2
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8
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(a) Cheng, C.-Y.; Tsai, H.-B.; Lin, M.-S. J. Heterocycl. Chem. 1995, 32, 73.
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Cheng, C.-Y.1
Tsai, H.-B.2
Lin, M.-S.3
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9
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(b) Murthy, A. R. K.; Chapman, J. M.; Wyrick, S. D.; Hall, I. H. Pharm. Res. 1986, 3, 286.
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Murthy, A.R.K.1
Chapman, J.M.2
Wyrick, S.D.3
Hall, I.H.4
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10
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84889504161
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note
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(c) The condensations may also be conveniently carried out in toluene or acetic acid at reflux. The addition of 0.1-0.3 mol equiv of DBU or Methylamine catalyzes the reaction in the aromatic hydrocarbon solvents.
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11
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84889501000
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Private communication from R. J. G. Searle, Shell Research Limited, Sittingbourne Research Centre, Sittingbourne, Kent, U.K.
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(a) Private communication from R. J. G. Searle, Shell Research Limited, Sittingbourne Research Centre, Sittingbourne, Kent, U.K.
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12
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84889544311
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(Shell Internationale Research Maatschappij B.V. Neth.). Neth. Appl., NL 8006568, 1981
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(b) Gilkerson, T. (Shell Internationale Research Maatschappij B.V. Neth.). Neth. Appl., NL 8006568, 1981.
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Gilkerson, T.1
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13
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84889503299
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(c) Koval'skaya, S. S.; Kozlov, N. G.; Shavyrin, S. V. Khim. Prir. Soedin. 1991, 29; Chem. Abstr. 1992, 116, 129270.
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Khim. Prir. Soedin.
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Koval'skaya, S.S.1
Kozlov, N.G.2
Shavyrin, S.V.3
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14
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84889542606
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(c) Koval'skaya, S. S.; Kozlov, N. G.; Shavyrin, S. V. Khim. Prir. Soedin. 1991, 29; Chem. Abstr. 1992, 116, 129270.
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Chem. Abstr.
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17
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84889543466
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note
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(a) Ethoxycarbonylation of homophthalic anhydride derivatives with this system is known. However, we are unaware of any reports describing the direct acylation of 1,3(2H, 4H)-dioxoisoquinolines (homophthalimides) 2 by this method, cf.:
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18
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84982076043
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(b) Chatterjea, J. N.; Mukherjee, S. K.; Bhakta, H. C. J.; Zilliken, F. Chem. Ber. 1980, 113, 3927.
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Chem. Ber.
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Chatterjea, J.N.1
Mukherjee, S.K.2
Bhakta, H.C.J.3
Zilliken, F.4
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21
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84889530842
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(Pfizer, Inc.). U.S. Patent 4569942, 1986
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(a) Kadin, S. (Pfizer, Inc.). U.S. Patent 4569942, 1986.
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Kadin, S.1
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22
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84889501787
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(Pfizer, Inc.). U.S. Patent 3998954, 1976
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(b) Kadin, S. (Pfizer, Inc.). U.S. Patent 3998954, 1976.
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Kadin, S.1
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24
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84889545934
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(Pfizer Co.). U.S. Patent 4730004, 1988
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(d) For application of this protocol to antinflammatory 1-acyl-2-oxindole-3-carboxamides, see: Kadin, S. (Pfizer Co.). U.S. Patent 4730004, 1988.
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Kadin, S.1
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25
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84889532787
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To the best of our knowledge, there exists no literature precedent for the 1,3-O- to C-acyl shift in the subject isoquinolinedione systems. However, similar acyl shifts have been successfully executed in a variety of other systems; cf.: (a) Lu, J. Q.; Wang, S. Y.; Zhang, P. Chin. Chem. Lett. 1992, 3, 337.
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(1992)
Chin. Chem. Lett.
, vol.3
, pp. 337
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Lu, J.Q.1
Wang, S.Y.2
Zhang, P.3
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27
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84987142847
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(c) Winkler, D. A.; Liepa, A. J.; Anderson-McKay, J. E.; Hart, N. K. Pestic. Sci. 1989, 27, 45.
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(1989)
Pestic. Sci.
, vol.27
, pp. 45
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Winkler, D.A.1
Liepa, A.J.2
Anderson-McKay, J.E.3
Hart, N.K.4
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28
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0003543593
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VCH Publishers: New York
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(d) For examples of the synthesis and O- to C-acyl shifts of enol esters to β-keto esters, see: Larock, R. C. Comprehensive Organic Transformations; VCH Publishers: New York, 1989; pp 743-744.
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(1989)
Comprehensive Organic Transformations
, pp. 743-744
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Larock, R.C.1
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32
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0003543593
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VCH Publishers: New York
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(b) For an excellent compilation of references on the subject of enolate hydroxylation, see: Larock, R. C. Comprehensive Organic Transformations; VCH Publishers: New York, 1989; pp 488-490.
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(1989)
Comprehensive Organic Transformations
, pp. 488-490
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Larock, R.C.1
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33
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84981379455
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2-Aryl-1,3,4-(2H)-trioxoisoquinolines, also known as phthalonimides, have been previously described; see: (a) Peterson, S.; Heitzer, H. Liebigs Ann. Chem. 1978, 283. (b) Buu-Hoi, N. P.; Saint-Ruf, G.; Bourgeade, J. C. J. Heterocycl. Chem. 1968, 5, 545. (c) Meyer, A.; Villenet, R. C. R. Hebd. Seances Acad. Sci. 1931, 193, 531, 1095.
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(1978)
Liebigs Ann. Chem.
, pp. 283
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Peterson, S.1
Heitzer, H.2
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34
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84981852733
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2-Aryl-1,3,4-(2H)-trioxoisoquinolines, also known as phthalonimides, have been previously described; see: (a) Peterson, S.; Heitzer, H. Liebigs Ann. Chem. 1978, 283. (b) Buu-Hoi, N. P.; Saint-Ruf, G.; Bourgeade, J. C. J. Heterocycl. Chem. 1968, 5, 545. (c) Meyer, A.; Villenet, R. C. R. Hebd. Seances Acad. Sci. 1931, 193, 531, 1095.
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J. Heterocycl. Chem.
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, pp. 545
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Buu-Hoi, N.P.1
Saint-Ruf, G.2
Bourgeade, J.C.3
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35
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84981452298
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2-Aryl-1,3,4-(2H)-trioxoisoquinolines, also known as phthalonimides, have been previously described; see: (a) Peterson, S.; Heitzer, H. Liebigs Ann. Chem. 1978, 283. (b) Buu-Hoi, N. P.; Saint-Ruf, G.; Bourgeade, J. C. J. Heterocycl. Chem. 1968, 5, 545. (c) Meyer, A.; Villenet, R. C. R. Hebd. Seances Acad. Sci. 1931, 193, 531, 1095.
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R. Hebd. Seances Acad. Sci.
, vol.193
, pp. 531
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Meyer, A.1
Villenet, R.C.2
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36
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33947092680
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(a) Vedejs, E.; Engler, D. A.; Telschow, J. E. J. Org. Chem. 1978, 43, 188.
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(1978)
J. Org. Chem.
, vol.43
, pp. 188
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Vedejs, E.1
Engler, D.A.2
Telschow, J.E.3
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37
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33847805672
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See also ref 13b
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(b) Vedejs, E. J. Am. Chem. Soc. 1974, 96, 5944. See also ref 13b.
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J. Am. Chem. Soc.
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Vedejs, E.1
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