Regioselective Anionic [3+2] Cyclizations of Imidazole Dinucleophiles with Oxaldiimidoyl Dichlorides − A Combined Experimental and Theoretical Study
2001; Wiley; Volume: 2001; Issue: 12 Linguagem: Inglês
10.1002/1099-0690(200106)2001
ISSN1434-193X
AutoresPeter Langer, Jörg Wuckelt, Manfred Döring, Peter R. Schreiner, Helmar Görls,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoEuropean Journal of Organic ChemistryVolume 2001, Issue 12 p. 2245-2255 Full Paper Regioselective Anionic [3+2] Cyclizations of Imidazole Dinucleophiles with Oxaldiimidoyl Dichlorides − A Combined Experimental and Theoretical Study Peter Langer, Peter Langer Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, GermanySearch for more papers by this authorJörg Wuckelt, Jörg Wuckelt Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this authorManfred Döring, Manfred Döring Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this authorPeter R. Schreiner, Peter R. Schreiner Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany Department of Chemistry, The University of Georgia, 1001 Cedar St., Athens, GA 30602-2556, USASearch for more papers by this authorHelmar Görls, Helmar Görls Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this author Peter Langer, Peter Langer Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, GermanySearch for more papers by this authorJörg Wuckelt, Jörg Wuckelt Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this authorManfred Döring, Manfred Döring Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this authorPeter R. Schreiner, Peter R. Schreiner Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany Department of Chemistry, The University of Georgia, 1001 Cedar St., Athens, GA 30602-2556, USASearch for more papers by this authorHelmar Görls, Helmar Görls Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this author First published: 15 May 2001 https://doi.org/10.1002/1099-0690(200106)2001:12 3.0.CO;2-CCitations: 15Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract Regioselective cyclization reactions between oxaldiimidoyl dichlorides and imidazole-derived dinucleophiles provide convenient access to biologically relevant diazabicyclo[2.2.1]heptanones, 1H-pyrrolo[1,2-a]benzimidazoles, 3H-imidazo[1,2-a]benzimidazoles and 2,3-dihydrothiazolo[3,2-a]benzimidazoles. All cyclizations proceed with good regioselectivity, directed by the heteroatoms of the dinucleophile. The tautomeric forms of the structurally mobile benzimidazoles have been studied both in solution and in the solid state. The structural properties and the regioselectivities are explained by semiempirical calculations. References 1 1a A. J. Charlson, J. S. Harrington , Carbohydr. Res. 1972 , 43 , 383 . − 10.1016/S0008-6215(00)83505-3 Web of Science®Google Scholar 3[1b] H. G. Alpermann , Arzneim.-Forsch. 1966 , 16 , 1641 . − CASWeb of Science®Google Scholar 4[1c] R. Zhou, E. B. Skibo , J. Med. Chem. 1996 , 39 , 4321 . 10.1021/jm960064d CASPubMedWeb of Science®Google Scholar 2 6[2a] P. Beak, J. L. Miesel , J. Am. Chem. Soc. 1967 , 84 , 2375 . − 10.1021/ja00986a024 Web of Science®Google Scholar 7[2b] G. P. Claxton, J. M. Grisar, N. L. Wiech , J. Med. Chem. 1974 , 17 , 364 . − 10.1021/jm00249a027 CASPubMedWeb of Science®Google Scholar 8[2c] J. H. M. Hill, T. R. Fogg, H. J. Guttmann , J. Org. Chem. 1975 , 40 , 2562 . 10.1021/jo00905a044 CASWeb of Science®Google Scholar 3 10[3a] M. D. Nair, R. Adams , J. Am. Chem. Soc. 1961 , 83 , 3518 . − 10.1021/ja01477a038 CASWeb of Science®Google Scholar 11[3b] R. Huisgen, H. Rist , Justus Liebigs Ann. Chem. 1955 , 594 , 159 . 10.1002/jlac.19555940205 CASWeb of Science®Google Scholar 4 For literature related to imidazoles and benzimidazoles, see: Google Scholar 13[4a] J. R. McClure, J. H. Custer, H. D. Schwarz, D. A. Lill , Synlett 2000 , 710 . − CASWeb of Science®Google Scholar 14[4b] A. R. Katritzky, C. N. Fali, J. Li , J. Org. Chem. 1997 , 62 , 4148 . 10.1021/jo9623191 CASWeb of Science®Google Scholar 5 For the extrusion of CO in the reaction between glycols and oxalyl dichloride, see: T. Iida, T. Itaya , Tetrahedron 1993 , 49 , 10511 . 10.1016/S0040-4020(01)81546-5 CASWeb of Science®Google Scholar 6 For cyclization reactions of dianions, see, for example: Google Scholar 17[6a] K. G. Bilyard, P. J. Garratt, R. Hunter, E. Lete , J. Org. Chem. 1982 , 47 , 4731 . − 10.1021/jo00145a024 CASWeb of Science®Google Scholar 18[6b] R. B. Bates, B. Gordon, T. K. Highsmith, J. J. White , J. Org. Chem. 1984 , 49 , 2981 . − 10.1021/jo00190a025 CASWeb of Science®Google Scholar 19[6c] K. Tanaka, H. Horiuchi, H. Yoda , J. Org. Chem. 1989 , 54 , 63 . − 10.1021/jo00262a020 CASWeb of Science®Google Scholar 20[6d] D. Seebach, M. Pohmakotr , Tetrahedron 1981 , 37 , 4047 . − 10.1016/S0040-4020(01)93280-6 CASWeb of Science®Google Scholar 21[6e] A. Maercker, A. Groos , Angew. Chem. 1996, 108, 216; Angew. Chem. Int. Ed. Engl. 1996 , 35 , 210 . − 10.1002/anie.199602101 CASWeb of Science®Google Scholar 22[6f] A. Maercker, M. Theis , Top. Curr. Chem. 1987 , 138 , 1 . − 10.1007/3-540-16931-8_7 CASGoogle Scholar 23[6g] J. Vollhardt, H.-J. Gais, L. Lukas , Angew. Chem. Int. Ed. Engl. 1985 , 24 , 608 . By “dianions” we refer to systems bearing two delocalized negative charges, the generation of which involves at least one abstraction of a proton attached to a carbon atom. 10.1002/anie.198506081 Web of Science®Google Scholar 7 For recent cyclization reactions between dianion equivalents and 1,2-dielectrophiles from our laboratory, see: Google Scholar 25[7a] P. Langer, E. Holtz , Angew. Chem. 2000, 112, 3208; Angew. Chem. Int. Ed. 2000 , 39 , 3086 . − 10.1002/1521-3773(20000901)39:17 3.0.CO;2-F CASPubMedWeb of Science®Google Scholar 26[7b] P. Langer, T. Eckardt , Angew. Chem. 2000, 112, 4503; Angew. Chem. Int. Ed. 2000 , 39 , 4343 . − 10.1002/1521-3773(20001201)39:23 3.0.CO;2-Q CASPubMedWeb of Science®Google Scholar 27[7c] P. Langer, T. Krummel , Chem. Commun. 2000 , 967 . − 10.1039/b001529f CASWeb of Science®Google Scholar 28[7d] P. Langer, I. Freifeld, E. Holtz , Synlett 2000 , 501 . − CASWeb of Science®Google Scholar 29[7e] P. Langer, I. Freifeld , Chem. Eur. J. 2001 , 7 , 565 . − 10.1002/1521-3765(20010202)7:3 3.0.CO;2-E CASPubMedWeb of Science®Google Scholar 30[7f] P. Langer, T. Schneider , Synlett 2000 , 497 . − CASWeb of Science®Google Scholar 31[7g] P. Langer, J. Wuckelt, M. Döring , J. Org. Chem. 2000 , 65 , 729 . − 10.1021/jo991377u CASWeb of Science®Google Scholar 32[7h] P. Langer, J. Wuckelt, M. Döring, H. Görls , J. Org. Chem. 2000 , 65 , 3603 . − 10.1021/jo991701l CASPubMedWeb of Science®Google Scholar 33[7i] P. Langer, I. Karimé , Synlett 2000 , 743 . − CASWeb of Science®Google Scholar 34[7j] P. Langer, V. Köhler , Org. Lett. 2000 , 1597 . − 10.1021/ol005852i CASPubMedWeb of Science®Google Scholar 35[7k] P. Langer, B. Kracke , Tetrahedron Lett. 2000 , 4545 . − 10.1016/S0040-4039(00)00682-1 CASWeb of Science®Google Scholar 36[7l] P. Langer, M. Döring, D. Seyferth , Synlett 1999 , 135 . − 10.1055/s-1999-2537 CASWeb of Science®Google Scholar 37[7m] P. Langer, M. Döring , Chem. Commun. 1999 , 2439 . − 10.1039/a906913e CASWeb of Science®Google Scholar 38[7n] P. Langer , Chem. Commun. 1999 , 1217 . − 10.1039/a901208g CASWeb of Science®Google Scholar 39[7o] P. Langer, J. Wuckelt, M. Döring, R. Beckert , Eur. J. Org. Chem. 1998 , 1467 . − 10.1002/(SICI)1099-0690(199807)1998:7 3.0.CO;2-H CASWeb of Science®Google Scholar 40[7p] P. Langer, M. Döring, D. Seyferth , Chem. Commun. 1998 , 1927 . − 10.1039/a803040e CASWeb of Science®Google Scholar 41[7q] P. Langer, M. Döring , Synlett 1998 , 396 . − 10.1055/s-1998-1671 CASWeb of Science®Google Scholar 42[7r] P. Langer, M. Döring , Synlett 1998 , 399 . 10.1055/s-1998-1673 CASWeb of Science®Google Scholar 8 44[8a] P. Langer , M. Stoll , Angew. Chem. 1999, 111, 1919; Angew. Chem. Int. Ed. 1999 , 38 , 1803 . − 10.1002/(SICI)1521-3773(19990614)38:12 3.0.CO;2-5 CASPubMedWeb of Science®Google Scholar 45[8b] P. Langer, T. Schneider, M. Stoll , Chem. Eur. J. 2000 , 6 , 3204 . − Google Scholar 46[8c] P. Langer, T. Eckardt , Synlett 2000 , 844 . − CASWeb of Science®Google Scholar 47[8d] P. Langer, N. N. R. Saleh , Org. Lett. 2000 , 3333 . 10.1021/ol006419b CASPubMedWeb of Science®Google Scholar 9 D. Lindauer, R. Beckert, M. Döring, P. Fehling, H. Görls , J. Prakt. Chem. 1995 , 337 , 143 . 10.1002/prac.19953370130 CASWeb of Science®Google Scholar 10 1H-Pyrrolo[1,2-a]benzimidazol-1-ones have previously been prepared by a different approach: W. Ried, H. Knorr , Justus Liebigs Ann. Chem. 1976 , 284 . 10.1002/jlac.197619760210 CASWeb of Science®Google Scholar 11 51[11a] For the preparation of a 2-hydroxy-1H-imidazo[1,2-a]imidazol-1-one, see: M. Smionar , Chem. Heterocycl. Compd. (Engl. Transl.) 1976 , 12 , 115 . − 10.1007/BF00570228 Google Scholar 52[11b] For 1H-imidazo[1,2-a]indoles: I. T. Forbes, H. K. A. Morgan, M. Thompson , Synth. Commun. 1996 , 26 , 745 . See also ref.[13b] 10.1080/00397919608086749 CASWeb of Science®Google Scholar 12 S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami, K. Tanabe , J. Am. Chem. Soc. 2000 , 3746 . 10.1021/ja993972j CASWeb of Science®Google Scholar 13 For related compounds, see: Google Scholar 55[13a] R. Beckert, M. Gruner , J. Prakt. Chem. 1992 , 334 , 611 . − 10.1002/prac.19923340711 CASWeb of Science®Google Scholar 56[13b] A. K. El-Shafei, H. S. Kashef, A.-B. A. G. Ghattas , Gazz. Chim. Ital. 1981 , 111 , 409 . CASGoogle Scholar 14 Only a very few bicyclic systems related to 12a−d have been reported previously: Google Scholar 58[14a] C. K. Ingold, S. D. Weaver , J. Chem. Soc. 1925 , 127 , 378 . − For the spectroscopic data of 1,3-dihydro-1,3-dimethyl-2H-benzimidazol-2-one, see: 10.1039/ct9252700378 CASWeb of Science®Google Scholar 59[14b] H. Quast, S. Ivanova, E.-M. Peters, K. Peters, H. G. von Schnering , Liebigs Ann. 1996 , 1541 . − 10.1002/jlac.199619961008 CASWeb of Science®Google Scholar 60[14c] For hericenes, see: P. Vogel, in Theoretically interesting Molecules, vol. 1 (Ed.: R. P. Thummel), JAI Press, Greenwich, CT, USA, 1989, p. 201. Google Scholar 15 M. S. Ashwood, A. W. Gibson, P. G. Houghton, G. R. Humphrey, D. C. Roberts, S. H. B. Wright , J. Chem. Soc., Perkin Trans. 1 1995 , 641 . 10.1039/p19950000641 CASWeb of Science®Google Scholar 16 M. Kato, S. Nishino, K. Ito, H. Yamakuni, H. Takasugi , Chem. Pharm. Bull. 1995 , 43 , 1358 . 10.1248/cpb.43.1358 CASPubMedWeb of Science®Google Scholar 17 R. M. Snider , Science 1991 , 251 , 435 . 10.1126/science.1703323 CASPubMedWeb of Science®Google Scholar 18 H. M. R. Hoffmann, J. Rabe , Angew. Chem. 1983, 95, 795; Angew. Chem. Int. Ed. Engl. 1983 , 22 , 795 . 10.1002/anie.198307951 Web of Science®Google Scholar 19 66[19a] R. Gompper, H.-U. Wagner , Angew. Chem. Int. Ed. Engl. 1988 , 27 , 1437 . − 10.1002/anie.198814371 Web of Science®Google Scholar 67[19b] F. Effenberger, H. Schlosser, P. Bäuerle, S. Maier, H. Port, H. C. Wolf , Angew. Chem. Int. Ed. Engl. 1988 , 27 , 281 . − 10.1002/anie.198802811 Web of Science®Google Scholar 68[19c] J. Fabian, H. Nakazumi, M. Matsuoka , Chem. Rev. 1992 , 92 , 1197 . − 10.1021/cr00014a003 CASWeb of Science®Google Scholar 69[19d] Z. Riedl, G. Hajós, A. Messmer, A. Rockenbauer, L. Korecz, G. Kollenz, W. M. F. Fabian, K. Peters, E.-M. Peters , Chem. Commun. 1997 , 757 . 10.1039/a608344g CASWeb of Science®Google Scholar 20 Further details of the crystal structure investigations are available on requests from the Cambridge Crystallographic Data Centre CCDC (12 Union Road, Cambridge CB2 1EZ, UK), on quoting the depository numbers CSD-132364 (6c), -132365 (7a), -132366 (8b), the names of the authors, and the journal citation. Google Scholar 21 MOLEN, An Interactive Structure Solution Procedure, Enraf−Nonius, Delft, The Netherlands, 1990. Google Scholar 22 G. M. Sheldrick , Acta Crystallogr., Sect. A 1990 , 46 , 467 . 10.1107/S0108767390000277 Google Scholar 23 G. M. Sheldrick, University of Göttingen, Germany, 1993. Google Scholar 24 J. J. P. Stewart, “AM1”, in The Encyclopedia of Computational Chemistry (Eds.: P. v. R. Schleyer, N. L. Allinger, T. Clark, J. Gasteiger, P. Kollman, H. F. Schaefer III, P. R. Schreiner), John Wiley & Sons, Chichester, 1998, pp. 2574. Google Scholar 25 J. A. Pople et al., Gaussian 98, Revision A.5, Gaussian, Inc., Pittsburgh PA, 1998. Google Scholar Citing Literature Volume2001, Issue12June 2001Pages 2245-2255 ReferencesRelatedInformation
Referência(s)