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Volumn 61, Issue 22, 1996, Pages 7967-7972

An efficient synthetic route to ethyl 2-aryl-4-hydroxy-1,3(2H,4H)-dioxoisoquinoline-4-carboxylates

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE;

EID: 0029848073     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961135j     Document Type: Article
Times cited : (21)

References (40)
  • 1
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    • D'Amico, J. J. (Monsanto Co.). U.S. Patent 4097260, 1978.
    • D'Amico, J.J.1
  • 10
    • 84889504161 scopus 로고    scopus 로고
    • note
    • (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.
  • 11
    • 84889501000 scopus 로고    scopus 로고
    • Private communication from R. J. G. Searle, Shell Research Limited, Sittingbourne Research Centre, Sittingbourne, Kent, U.K.
    • (a) Private communication from R. J. G. Searle, Shell Research Limited, Sittingbourne Research Centre, Sittingbourne, Kent, U.K.
  • 12
    • 84889544311 scopus 로고    scopus 로고
    • (Shell Internationale Research Maatschappij B.V. Neth.). Neth. Appl., NL 8006568, 1981
    • (b) Gilkerson, T. (Shell Internationale Research Maatschappij B.V. Neth.). Neth. Appl., NL 8006568, 1981.
    • Gilkerson, T.1
  • 14
    • 84889542606 scopus 로고
    • (c) Koval'skaya, S. S.; Kozlov, N. G.; Shavyrin, S. V. Khim. Prir. Soedin. 1991, 29; Chem. Abstr. 1992, 116, 129270.
    • (1992) Chem. Abstr. , vol.116 , pp. 129270
  • 17
    • 84889543466 scopus 로고    scopus 로고
    • note
    • (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.:
  • 21
    • 84889530842 scopus 로고    scopus 로고
    • (Pfizer, Inc.). U.S. Patent 4569942, 1986
    • (a) Kadin, S. (Pfizer, Inc.). U.S. Patent 4569942, 1986.
    • Kadin, S.1
  • 22
    • 84889501787 scopus 로고    scopus 로고
    • (Pfizer, Inc.). U.S. Patent 3998954, 1976
    • (b) Kadin, S. (Pfizer, Inc.). U.S. Patent 3998954, 1976.
    • Kadin, S.1
  • 24
    • 84889545934 scopus 로고    scopus 로고
    • (Pfizer Co.). U.S. Patent 4730004, 1988
    • (d) For application of this protocol to antinflammatory 1-acyl-2-oxindole-3-carboxamides, see: Kadin, S. (Pfizer Co.). U.S. Patent 4730004, 1988.
    • Kadin, S.1
  • 25
    • 84889532787 scopus 로고
    • 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.
    • (1992) Chin. Chem. Lett. , vol.3 , pp. 337
    • Lu, J.Q.1    Wang, S.Y.2    Zhang, P.3
  • 28
    • 0003543593 scopus 로고
    • VCH Publishers: New York
    • (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.
    • (1989) Comprehensive Organic Transformations , pp. 743-744
    • Larock, R.C.1
  • 32
    • 0003543593 scopus 로고
    • VCH Publishers: New York
    • (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.
    • (1989) Comprehensive Organic Transformations , pp. 488-490
    • Larock, R.C.1
  • 33
    • 84981379455 scopus 로고
    • 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.
    • (1978) Liebigs Ann. Chem. , pp. 283
    • Peterson, S.1    Heitzer, H.2
  • 34
    • 84981852733 scopus 로고
    • 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.
    • (1968) J. Heterocycl. Chem. , vol.5 , pp. 545
    • Buu-Hoi, N.P.1    Saint-Ruf, G.2    Bourgeade, J.C.3
  • 35
    • 84981452298 scopus 로고
    • 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.
    • (1931) R. Hebd. Seances Acad. Sci. , vol.193 , pp. 531
    • Meyer, A.1    Villenet, R.C.2
  • 37
    • 33847805672 scopus 로고
    • See also ref 13b
    • (b) Vedejs, E. J. Am. Chem. Soc. 1974, 96, 5944. See also ref 13b.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 5944
    • Vedejs, E.1


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