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Volumn 63, Issue 6, 1998, Pages 1863-1871

Palladium-Catalyzed Heteroannulation Leading to Heterocyclic Structures with Two Heteroatoms: A Highly Convenient and Facile Method for a Totally Regio- and Stereoselective Synthesis of (Z)-2,3-Dihydro-2-(ylidene)-1,4-benzo- and -naphtho [2,3-b]dioxins

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZODIOXIN DERIVATIVE; 2,3 DIHYDRO 2 (YLIDENE) 1,4 BENZO[2,3 B]DIOXIN; 2,3 DIHYDRO 2 (YLIDENE) 1,4 NAPHTHO[2,3 B]DIOXIN; 2,3 DIHYDRO 2 [(2',4' DIOXO 1',2',3',4' TETRAHYDROPYRIMIDIN 5 YL)METHYLIDENE] 1,4 BENZODIOXIN; COPPER; PALLADIUM; THYMIDYLATE SYNTHASE INHIBITOR; TRIETHYLAMINE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

EID: 0032549587     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9717595     Document Type: Article
Times cited : (85)

References (98)
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    • 3N, employing the reaction condition of our heteroannulation process resulted in no coupled product. Only the deiodinated product was obtained. This could be explained first by oxidative coupling followed by reduction of the palladated complex by triethylamine. We thank a referee in pointing this out.
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    • In case of (E)- and (Z)-isomers, different chemical shift values of vinylic proton of exocyclic double bond due to the deshielding effect of oxygen of some heterocyclic rings have been invoked to account for the results: (a) Jager, V.; Gunther, H. J. Tetrahedron Lett. 1977, 2543. (b) Yamamoto, M. J. Chem. Soc., Chem. Commun. 1978, 649. (c) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976.
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    • In case of (E)- and (Z)-isomers, different chemical shift values of vinylic proton of exocyclic double bond due to the deshielding effect of oxygen of some heterocyclic rings have been invoked to account for the results: (a) Jager, V.; Gunther, H. J. Tetrahedron Lett. 1977, 2543. (b) Yamamoto, M. J. Chem. Soc., Chem. Commun. 1978, 649. (c) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976.
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    • In case of (E)- and (Z)-isomers, different chemical shift values of vinylic proton of exocyclic double bond due to the deshielding effect of oxygen of some heterocyclic rings have been invoked to account for the results: (a) Jager, V.; Gunther, H. J. Tetrahedron Lett. 1977, 2543. (b) Yamamoto, M. J. Chem. Soc., Chem. Commun. 1978, 649. (c) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976.
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    • note
    • X-ray data of compound 31 has been deposited at Cambridge Cystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
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    • The coordination between palladium and oxygen or other heteroatom is well precedented in the literature: (a) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (b) Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Namkoong, E.-Y.; Kim, T.-H. Tetrahedron Lett 1995, 36, 6287. (c) Bernocchi, E,; Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G, Tetrahedron Lett. 1992, 33, 3073. (d) Chiusoli, G. P.; Costa, M.; Pergreffi, P.; Reverberi, S.; Salerno, G. Giazz. Chim. Ital. 1985, 115, 691.
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    • The coordination between palladium and oxygen or other heteroatom is well precedented in the literature: (a) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (b) Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Namkoong, E.-Y.; Kim, T.-H. Tetrahedron Lett 1995, 36, 6287. (c) Bernocchi, E,; Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G, Tetrahedron Lett. 1992, 33, 3073. (d) Chiusoli, G. P.; Costa, M.; Pergreffi, P.; Reverberi, S.; Salerno, G. Giazz. Chim. Ital. 1985, 115, 691.
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    • The coordination between palladium and oxygen or other heteroatom is well precedented in the literature: (a) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (b) Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Namkoong, E.-Y.; Kim, T.-H. Tetrahedron Lett 1995, 36, 6287. (c) Bernocchi, E,; Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G, Tetrahedron Lett. 1992, 33, 3073. (d) Chiusoli, G. P.; Costa, M.; Pergreffi, P.; Reverberi, S.; Salerno, G. Giazz. Chim. Ital. 1985, 115, 691.
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    • The coordination between palladium and oxygen or other heteroatom is well precedented in the literature: (a) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (b) Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Namkoong, E.-Y.; Kim, T.-H. Tetrahedron Lett 1995, 36, 6287. (c) Bernocchi, E,; Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G, Tetrahedron Lett. 1992, 33, 3073. (d) Chiusoli, G. P.; Costa, M.; Pergreffi, P.; Reverberi, S.; Salerno, G. Giazz. Chim. Ital. 1985, 115, 691.
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    • note
    • 3)4 (40 mg, 0.035 mmol), no cyclized product 3i was obtained.
  • 90
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    • note
    • Although a referee suggested that path b is the most probable path for the formation of the products 3, we, however, do not preclude path a in the stereoselective formation of the products 3.
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    • note
    • -1].
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    • The biological activity of compound 12 is under study and will be reported elsewhere
    • The biological activity of compound 12 is under study and will be reported elsewhere.


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