Synthesis of 2,3‐dihydro‐I H,4 H, 6 H‐furo[3,4‐b]pyrrolo[1,2‐a]quinoline‐6a(7H)‐carbonitrile; a novel type of intramolecular tetrahydrofuran formation / Verboom W., Morzherin Y., Kelderman E., Engbersen J.F.J., Reinhoudt D.N., van Hummel G.J., Harkema S. // Recueil des Travaux Chimiques des Pays‐Bas. - 1993. - V. 112, l. 10. - P. 549-551.

ISSN:
01650513
Type:
Article
Abstract:
Appropriately 4‐substituted 1,2,3,3a,4,5‐hexahydro‐3a‐(methoxymethyl)pyrrolo[1,2‐a]quinolines 3 cyclize to 2,3‐dihydro‐1 H,4H,6H‐furo[3,4‐b]pyrrolo[1,2‐a]quinoline‐6a(7H)‐carbonitrile (5) upon heating in polar solvents, the reaction being accelerated by lithium bromide. The formation of the annulated tetrahydrofuran ring of 5 takes place via intramolecular attack of the oxygen atom of the methoxymethyl substituent at C‐3a on the electrophilic carbon atom at C‐4. The structure of 5 was confirmed by single‐crystal X‐ray structure determination. Copyright © 1993 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
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DOI:
10.1002/recl.19931121006
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Affiliations Laboratories of Organic Chemistry, University of Twente, P.O. Box 217, Enschede, 7500 AE, Netherlands; Laboratories of Chemical Physics, University of Twente, P.O. Box 217, Enschede, 7500 AE, Netherlands
References Meth‐Cohn, O., Suschitzky, H., (1972) Adv. Heterocycl. Chem., 14, p. 211; Verboom, W., Reinhoudt, D.N., (1990) Recl. Trav. Chim. Pays‐Bas, 109, p. 311; Verboom, W., Reinhoudt, D.N., Visser, R., Harkema, S., (1984) J. Org. Chem., 49, p. 269; Groenen, L.C., Verboom, W., Nijhuis, W.H.N., Reinhoudt, D.N., van Hummel, G.J., Feil, D., (1988) Tetrahedron, 44, p. 4637; Nijhuis, W.H.N., Verboom, W., El‐Fadl, Harkema, S., Reinhoudt, D.N., (1989) J. Org. Chem., 54, p. 199; Nijhuis, W.H.N., Verboom, W., Reinhoudt, D.N., Harkema, S., (1987) J. Am. Chem. Soc., 109, p. 3136; Nijhuis, W.H.N., Verboom, W., El‐Fadl, van Hummel, G.J., Reinhoudt, D.N., (1989) J. Org. Chem., 54, p. 209; Kelderman, E., Noorlander‐Bunt, H.G., van Eerden, J., Verboom, W., Reinhoudt, D.N., (1991) Recl. Trav. Chim. Pays‐Bas, 110, p. 115; Kelderman, E., Verboom, W., Engbersen, J.F.J., Harkema, S., Heesink, G.J.T., Lehmusvaara, E., van Hulst, N.F., Reinhoudt, D.N., (1992) Chem. Mater., 4, p. 626; Soai, K., Oyamada, H., Ookawa, A., (1982) Synth. Commun., 12, p. 463; The optical purity of 2 was established using 10 equiv of Eu(hfc)3 {tris[3‐(heptafluoropropyl)hydroxymethylene]‐(–)‐camphorato europium(III)} and 10 equiv of AgFOD [(6,6,7,7,8,8,8‐heptafluoro‐2,2‐dimethyl‐3,5‐octanedionato)‐silver]. The 1H‐NMR spectrum of (&)2 showed a doubling of the OCH3 singlet; The optical purity of 3a was established using 1.0 equiv of Eu(hfc)3 and 1.0 equiv of AgFOD. The 1H‐NMR spectrum of (&)3a exhibited a doubling of the signals of the OCH2 and SMe groups; The optical purity of 5 was established using 0.1 equiv of Eu(hfc)3. The 1H‐NMR spectrum of (&)‐5 showed a doubling of the OCH2 groups at C‐4 and C‐6; (1973) Rodd's Chemistry of Carbon Compounds, 4. , S. Coffey, Elsevier, Amsterdam, 2nd ed., part a; Kröper, H., (1965) Methoden der Organischen Chemie, 4 (3). , (Houben‐Weyl), Georg Thieme Verlag, Stuttgart, band; Stevens, D.R., Till, C.P., Whiting, D.A., (1992), p. 185. , For a recent example, see:, J. Chem. Soc., Perkin Trans. 1; The presence of solvent was proven by 1H‐NMR spectroscopy; (1983) Structure Determination Package, , B. A. Frenz and Associates Inc., College Station, TX, and Enraf‐Nonius, Delft; Details of the structure are deposited with the Cambridge Structural Database
Correspondence Address Verboom, W.; Laboratories of Organic Chemistry, University of Twente, P.O. Box 217, Enschede, 7500 AE, Netherlands
Language of Original Document English
Source Scopus