Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence
A convenient methodology for the synthesis of 3-sustituted-2,3- dihydrobenzofurans was developed based on the tandem intramolecular carbolithiation-cyclization of 2-bromophenyl-3-phenylprop-2-enyl ether, followed by trapping of the new lithiated intermediate by suitable electrophiles. Several electr...
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2014
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| 001 | PAPER-14280 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204446.0 | ||
| 008 | 190411s2014 xx ||||fo|||| 00| 0 eng|d | ||
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| 100 | 1 | |a Rodríguez, C. | |
| 245 | 1 | 0 | |a Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence |
| 260 | |c 2014 | ||
| 270 | 1 | 0 | |m Nudelman, N.S.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EGA Buenos Aires, Argentina; email: nudelman@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Vázquez A.J.De Waisbaum R.G.Nudelman, N.S., Organolithiums as useful synthetic intermediates for tandem reactions (2006) The Chemistry of Organolithium Compounds, pp. 63-137. , John Wiley & Sons: New York | ||
| 504 | |a Hogan, A.M.L., O'Shea, D.F., (2008) Chem. Commun., 33, pp. 3839-3851 | ||
| 504 | |a Girard, A.-L., Lhermet, R., Fressigné, C., Durandetti, M., Maddaluno, J., (2012) Eur. J. Org. Chem., pp. 2895-2905 | ||
| 504 | |a Clayden, J., (2002) Organolithium Selective for Synthesis;, 23. , Tetrahedron Organic Chemistry: Oxford | ||
| 504 | |a Mealy, M.J., Bailey, W.F., (2002) J. Organomet. Chem., 646, pp. 59-67 | ||
| 504 | |a Kizirian, J.-C., (2008) Chem. Rev., 108, pp. 140-205 | ||
| 504 | |a Garća, G.V., Nudelman, N.S., (2003) Org. Prep. Proced. Int., 35, pp. 447-500 | ||
| 504 | |a Nudelman, N.S., Garća, G.V., (2001) J. Org. Chem., 66, pp. 1387-1394 | ||
| 504 | |a Sefkow, M., (2003) Synthesis, pp. 2595-2625 | ||
| 504 | |a Bailey, W.F., Punzalan, E.R., (1996) Tetrahedron Lett., 37, pp. 5435-5436 | ||
| 504 | |a Newcomb, M., Choi, S.-Y., Horner, J.H., (1999) J. Org. Chem., 64, pp. 1225-1231 | ||
| 504 | |a Bodineau, N., Nudelman, N.S., Garća, G.V., Mattalia, J.-M., Martins, R., Arbelot, M., Chanon, M., (2002) Arkivoc, pp. 139-150 | ||
| 504 | |a Garcia, G., (2002), PhD Thesis, Universidad de Buenos Aires Buenos Aires; Rodŕguez, C., Vázquez, A.J., Nudelman, N.S., (2010) J. Phys. Org. Chem., 23, pp. 978-984 | ||
| 504 | |a Boche, G., Schimeczek, M., Cioslowski, J., Piskorz, P., (1998) Eur. J. Org. Chem., pp. 1851-1860 | ||
| 504 | |a Ribéreau, P., Delamare, M., Célanire, S., Quéguiner, G., (2001) Tetrahedron Lett., 42, pp. 3571-3573 | ||
| 504 | |a Shriver, D.F., Drezdzon, M.A., (1986) The Manipulation of Air-Sensitive Compounds, p. 336. , 2nd ed.; John Wiley and Sons: New York | ||
| 504 | |a Nudelman, N.S., Garća Liñares, G.E., (2000) J. Org. Chem., 65, pp. 1629-1635 | ||
| 504 | |a Bodineau, N., Mattalia, J.-M., Thimokhin, V., Handoo, K., Négrel, J.-C., Chanon, M., (2000) Org. Lett., 2, pp. 2303-2306 | ||
| 520 | 3 | |a A convenient methodology for the synthesis of 3-sustituted-2,3- dihydrobenzofurans was developed based on the tandem intramolecular carbolithiation-cyclization of 2-bromophenyl-3-phenylprop-2-enyl ether, followed by trapping of the new lithiated intermediate by suitable electrophiles. Several electrophiles were tested, affording good to excellent yields. Alkyl bromides show better results than chlorides and when doubly halogenated alkyl chains are used as electrophiles only one position reacts, affording substituted benzofurans conveniently functionalized to undergo further reactions. The performance of both butyl and phenyllithium as lithiating agents was examined. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] © 2014 Taylor and Francis Group, LLC. |l eng | |
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EGA Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ALKYLATION |
| 690 | 1 | 0 | |a BENZOFURANS |
| 690 | 1 | 0 | |a INTRAMOLECULAR CARBOCYCLIZATION |
| 690 | 1 | 0 | |a INTRAMOLECULAR CARBOLITHIATION |
| 690 | 1 | 0 | |a ORGANOLITHIUM |
| 700 | 1 | |a Nudelman, N.S. | |
| 773 | 0 | |d 2014 |g v. 44 |h pp. 772-778 |k n. 6 |p Synth. Commun. |x 00397911 |t Synthetic Communications | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-84894454250&doi=10.1080%2f00397911.2013.830132&partnerID=40&md5=7a49561c3386de4e7fb1daf24bc3975a |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1080/00397911.2013.830132 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00397911_v44_n6_p772_Rodriguez |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397911_v44_n6_p772_Rodriguez |y Registro en la Biblioteca Digital |
| 961 | |a paper_00397911_v44_n6_p772_Rodriguez |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 75233 | ||