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European Journal of Organic Chemistry
Volumn , Issue 28, 2011, Pages 5626-5635
Versatile synthesis of isoquinolines and isochromenes by Pd-catalyzed oxidative carbonylation of (2-alkynyl)benzylideneamine derivatives
Author keywords

Alkynes; Carbonylation; Cyclization; High pressure chemistry; Palladium
Indexed keywords

EID: 80053193611     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100739     Document Type: Article
Times cited : (24)
References (76)
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    • For recent examples of formation of isoquinoline-3-carboxylic esters starting from acyclic precursors, see: T. Gerfaud, L. Neuville, J. Zhu, Angew. Chem. Int. Ed. 2009, 48, 572-577.
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    • Gerfaud, T.1    Neuville, L.2    Zhu, J.3
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    • To the best of our knowledge, the only examples reported so far of the synthesis of isoquinolin-4-carboxylic esters by a carbonylative approach were based on Pd-catalyzed alkoxycarbonylation of 4-bromoisoquinolines, see: R. A. Head, A. Ibbotson, Tetrahedron Lett. 1984, 25, 5939-5942.
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    • Head, R.A.1    Ibbotson, A.2
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    • For representative examples of pharmacologically active isoquinoline-3-carboxylic derivatives, see: K. H. Huang, J. Veal, T. Barta, E. D. Smith, W. Ma, A. Ommen, U. S. Patent 2008070935 A1, 2008.
    • (2008)
    • Huang, K.H.1    Veal, J.2    Barta, T.3    Smith, E.D.4    Ma, W.5    Ommen, A.6
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    • Grayson M. Eckroth D. Bushey G.J. Campbell L. Klingsberg A. Van Nes) L. These conditions (16 atm of CO together with 5 atm total of air, considering that the autoclave was loaded under 1 atm of air) corresponded to 76.2 % of CO in air and were outside the explosion limits for CO in air (ca. 16-70 % at 18-20 °C and atmospheric pressure, 14.8-71.4 % at 100 °C and atmospheric pressure). At higher total pressure, the range of flammability decreases: for example, at 20 atm and 20 °C the limits are ca. 19 % and 60 %; see:, in:, 3rd ed., 4 (Eds.:, Wiley-Interscience, New York
    • These conditions (16 atm of CO together with 5 atm total of air, considering that the autoclave was loaded under 1 atm of air) corresponded to 76.2 % of CO in air and were outside the explosion limits for CO in air (ca. 16-70 % at 18-20 °C and atmospheric pressure, 14.8-71.4 % at 100 °C and atmospheric pressure). At higher total pressure, the range of flammability decreases: for example, at 20 atm and 20 °C the limits are ca. 19 % and 60 %; see:, C. M. Bartish, G. M. Drissel, in: Kirk-Othmer Encyclopedia of Chemical Technology, 3rd ed., vol. 4 (Eds.:, M. Grayson, D. Eckroth, G. J. Bushey, L. Campbell, A. Klingsberg, L. van Nes), Wiley-Interscience, New York, 1978, p. 775.
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    • The isochromene core is present in several naturally occurring and biologically active compounds; for recent examples, see: C. Shao, C. Wang, C. Zheng, Z. She, Y. Lin, Y. Gu, Nat. Prod. Res. 2010, 24, 81-85.
    • (2010) Nat. Prod. Res. , vol.24 , pp. 81-85
    • Shao, C.1    Wang, C.2    Zheng, C.3    She, Z.4    Lin, Y.5    Gu, Y.6
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    • We have previously shown that isochromene-4-carboxylic ester derivatives 4 could be obtained in moderate to fair yields by Pd-catalyzed oxidative carbonylation of 2-alkynylbenzaldehydes, after a prolonged reaction time (24 h). However, the desired product was usually obtained as a mixture with other by-products. Moreover, the method did not work with substrates bearing a bulky substituent on the triple bond (such as 5c), whereas in the case of 2-alkynylphenyl ketones (such as 5d) the reaction selectively afforded dihydroisobenzofuran derivatives rather than isochromenes 4; see.
    • We have previously shown that isochromene-4-carboxylic ester derivatives 4 could be obtained in moderate to fair yields by Pd-catalyzed oxidative carbonylation of 2-alkynylbenzaldehydes, after a prolonged reaction time (24 h). However, the desired product was usually obtained as a mixture with other by-products. Moreover, the method did not work with substrates bearing a bulky substituent on the triple bond (such as 5c), whereas in the case of 2-alkynylphenyl ketones (such as 5d) the reaction selectively afforded dihydroisobenzofuran derivatives rather than isochromenes 4; see:, A. Bacchi, M. Costa, N. Della Cà, M. Fabbricatore, A. Fazio, B. Gabriele, C. Nasi, G. Salerno, Eur. J. Org. Chem. 2004, 574-585.
    • (2004) Eur. J. Org. Chem. , pp. 574-585
    • Bacchi, A.1    Costa, M.2    Della Cà, N.3    Fabbricatore, M.4    Fazio, A.5    Gabriele, B.6    Nasi, C.7    Salerno, G.8
  • 74

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.