View Item 

Show simple item record

Reactions of Azides with Electrophiles: New Methods for the Generation of Cationic 2‐Azabutadienes. Synthesis of 1,2, 3,4‐Tetrahydroquinolines and 1,2‐Dihydroquinolines via a Hetero Diels–Alder Reaction
dc.contributor.authorPearson, William H.en_US
dc.contributor.authorFang, Wen‐kuien_US
dc.date.accessioned2013-12-04T18:56:48Z
dc.date.available2013-12-04T18:56:48Z
dc.date.issued1997en_US
dc.identifier.citationPearson, William H.; Fang, Wen‐kui (1997). "Reactions of Azides with Electrophiles: New Methods for the Generation of Cationic 2â Azabutadienes. Synthesis of 1,2, 3,4â Tetrahydroquinolines and 1,2â Dihydroquinolines via a Hetero Dielsâ Alder Reaction." Israel Journal of Chemistry 37(1): 39-46. <http://hdl.handle.net/2027.42/101768>en_US
dc.identifier.issn0021-2148en_US
dc.identifier.issn1869-5868en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/101768
dc.description.abstractTwo methods for the generation of iminium ions of the type ArN + (X)=CHR (X = H or alkyl, R = H or alkyl) are reported: (1) the Bronsted‐acid‐promoted rearrangement of benzylic azides and (2) the intermolecular Schmidt reactions of azides XN 3 (X = aliphatic) with benzylic carbocations derived from benzylic alcohols ArCH(R)OH. The iminium ions ArN + (X)=CHR behave as cationic 2‐azabutadienes in the presence of alkenes and alkynes, producing 1,2, 3,4‐tetrahydroquinolines and 1,2‐dihydroquinolines by a hetero Diels–Alder reaction.en_US
dc.publisherWILEY‐VCH Verlagen_US
dc.titleReactions of Azides with Electrophiles: New Methods for the Generation of Cationic 2‐Azabutadienes. Synthesis of 1,2, 3,4‐Tetrahydroquinolines and 1,2‐Dihydroquinolines via a Hetero Diels–Alder Reactionen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbtoplevelScienceen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109–1055, USAen_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/101768/1/199700007_ftp.pdf
dc.identifier.doi10.1002/ijch.199700007en_US
dc.identifier.sourceIsrael Journal of Chemistryen_US
dc.identifier.citedreference(a) Fishwick, C.W.G.; Storr, R.C.; Manley, P.W. J. Chem. Soc., Chem. Commun. 1984, 19, 1304 – 1305. (b) Blount, B.K.; Perkin, W.H.; Plant, S.G.P. J. Chem. Soc. 1929; 1975 – 1987.en_US
dc.identifier.citedreferenceMellor, J.M.; Merriman, G.D.; Riviere, P. Tetrahedron Lett. 1991, 32, 7103 – 7106.en_US
dc.identifier.citedreferenceBeifuss, U.; Ledderhose, S. J. Chem. Soc., Chem. Commun. 1995, 2137.en_US
dc.identifier.citedreferenceThis process may be desirable, such as in syntheses of the julolidines. 4c.7en_US
dc.identifier.citedreference(a) Mellor, J.M.; Rataj, H. Tetrahedron Lett. 1996, 37, 2619 – 2622. (b) Mellor, J.M.; Merriman, G.D.; Rataj, H.; Reid, G. Tetrahedron Lett. 1996, 37, 2615 – 2618.en_US
dc.identifier.citedreference(a) Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357 – 7360. (b) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256 – 2257. See also the earlier work by Kobayashi cited in these papers.en_US
dc.identifier.citedreferenceIn related work, Aubé has found that benzylic azides rearrange to N ‐aryl iminium ions in the presence of Lewis acids, and that these cationic 2‐azabutadienes may participate in Mannich‐type chemistry: J. Aubé (University of Kansas),personal communication.en_US
dc.identifier.citedreference(a) Pearson, W.H.; Schkeryantz, J.M. Tetrahedron Lett. 1992, 33, 5291 – 5294. (b) Pearson, W.H.; Walavalkar, R.; Schkeryantz, J.M.; Fang, W.‐k.; Blickensdorf, J.D. J. Am. Chem. Soc. 1993, 115, 10183 – 10194. (c) Pearson, W.H.; Fang, W.‐k. J. Org. Chem. 1995, 60, 4960 – 4961.en_US
dc.identifier.citedreferenceFor leading references on Aubé's related work on the intra‐ and intermolecular Schmidt reactions of azides with Lewis‐acid‐activated carbonyl compounds, see: (a) Aubé, J.; Milligan, G.L. J. Am. Chem. Soc. 1991, 113, 8965 – 8966. (b) Milligan, G.L.; Mossman, C.J.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 10449 – 10459.en_US
dc.identifier.citedreferenceMurphy, S.T.; Taylor, W.C.; Vadasz, A. Aust. J. Chem. 1982, 35, 1215.en_US
dc.identifier.citedreference(a) Abramovich, R.A.; Kyba, E.P. In The Chemistry of the Azido Group; Patai, S., ed.; John Wiley and Sons: London, 1971,pp 221 – 329. (b) Banthorpe, D.V. In The Chemistry of the Azido Group; Patai, S. Ed.; John Wiley and Sons: London, 1971,pp 397 – 440. (c) Abramovitch, R.A.; Jeyaraman, R. In Azides and Nitrenes: Reactivity and Utility; Scriven, E.F.V., ed.; Academic Press: Orlando, 1984,pp 297 – 357. (d) Smith, P.A.S. In Derivatives of Hydrazine and Other Hydronitrogens Having N‐N Bonds Benjamin/Cummings: London, 1983,pp 263 – 300. (e) Smith, P.A.S. In Molecular Rearrangements; de Mayo, P., Ed.; John Wiley and Sons: New York, 1963;Vol. 1,pp 457 – 591. For examples of the use of both the Bronsted‐ and Lewis‐acid‐catalyzed decomposition of azides to imines and/or iminium ions, see: (f) Trost, B.M.; Vaultier, M.; Santiago, M.L. J. Am. Chem. Soc. 1980, 102, 7929 – 7932 and (g) Tanino, K.; Takahashi, M.; Murayama, K.; Kuwajima, I. J. Org. Chem. 1992, 57, 7009 – 7010.en_US
dc.identifier.citedreferenceFor example, the Schmidt reaction of p ‐methoxybenzyl alcohol and α‐methyl‐ p ‐methoxybenzyl alcohol led to a mixture of iminium ions resulting from both aryl and hydrogen migration: 19cen_US
dc.identifier.citedreferenceGogte, V.N.; El‐Namaky, H.M.; Salama, M.A.; Tilik, B.D. Tetrahedron Lett. 1969, 3319 – 3320.en_US
dc.identifier.citedreferenceKatritzky, A.R.; Rachwal, B.; Rachwal, S. J. Org. Chem. 1993, 58, 812 – 813.en_US
dc.identifier.citedreferenceFor the spectral data of a similar compound, see: (a) Dicken, C.M.; Lu, F.‐L.; Bruice, T.C. Tetrahedron Lett. 1986, 27, 5967 – 5970. (b) Bruice, T.C.; Dicken, C.M.; Balasubramanian, P.N.; Woon, T.C.; Lu, F.‐L. J. Am. Chem. Soc. 1987, 109, 3436 – 3443.en_US
dc.identifier.citedreferenceFor the preparation and spectral data of a similar compound, 4‐methyltetrahydroquinoline, see: Kano, S.; Tanaka, Y.; Hibino, S. Heterocycles 1980, 14, 39 – 41.en_US
dc.identifier.citedreferenceProtiva, M.; Jilek, J.O.; Vejdelek, Z. J.; Exner, O. Chim. Listy 1952, 46 551 – 554, Chem. Abstr. 1954, 2710e.en_US
dc.identifier.citedreferenceThis azide was prepared by treating 1‐bromo‐1‐phenylethane with NaN 3 in DMSO overnight. See: Moss, R.A.;Jang, e.g.; Krogh‐Jespersen, K. Tetrahedron Lett. 1995, 36, 1409 – 1412.en_US
dc.identifier.citedreferenceSchweizer, E.D.; Goff, S.D.; Murray, W.P. J. Org. Chem. 1977, 42, 200 – 205.en_US
dc.identifier.citedreferenceLieber, E.; Chao, T.S.; Ramachandra Rao, C.N. J. Org. Chem. 1957, 22, 238 – 240.en_US
dc.identifier.citedreference(a) Boger, D.L.; Weinreb, S.M. Hetero Diels‐Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (b) Weinreb, S.M. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I., eds.; Pergamon Press: Oxford, 1991;Vol. 5,p 401.en_US
dc.identifier.citedreferenceFor a recent overview of the use of 2‐azabutadienes for tetrahydroquinoline synthesis, see: Mellor, J.M.; Merriman, G.D. Tetrahedron 1995, 51, 6115 – 6132.en_US
dc.identifier.citedreferenceGrigos, V.I.; Povarov, L.S.; Mikhailov, B.M. Izv. Akad. Nauk SSSR, Ser. Khim. 1965, 12, 2163. Povarov, L. Usp. Khim. 1967, 36, 1533.en_US
dc.identifier.citedreference(a) Katritzky, A.R.; Rachwal, B.; Rachwal, S. J. Org. Chem. 1995, 60, 2588 – 2596. (b) Katritzky, A.R.; Rachwal, B.; Rachwal, S. J. Org. Chem. 1995, 60, 3993 – 4001. (c) Katritzky, A.R.; Rachwal, B.; Rachwal, S.; Abboud, K.A. J. Org. Chem. 1996, 61, 3117 – 3126. See also earlier work by Katritzky cited in these papers.en_US
dc.identifier.citedreferenceSwann, G.A. J. Chem. Soc., Chem. Commun. 1969, 20.en_US
dc.identifier.citedreferenceHesse, K.‐D. Liebigs Ann. Chem. 1970, 741, 117 – 123.en_US
dc.identifier.citedreferenceShono, T.; Matsumura, Y.; Inoue, K.; Ohmizu, H.; Kashimura, S. J. Am. Chem. Soc. 1982, 104, 5753 – 5757.en_US
dc.identifier.citedreferenceKametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385 – 3395.en_US
dc.identifier.citedreferenceGrieco, P.A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855 – 5858.en_US
dc.identifier.citedreferenceBorrione, E.; Prato, M.; Scorrano, G.; Stivanello, M. J. Chem. Soc., Perkin Trans. 1 1989, 2245 – 2250 and earlier work cited therein.en_US
dc.identifier.citedreferenceBeifuss, U.; Kunz, O.; Ledderhose, S.; Taraschewski, M.; Tonko, C. Synlett 1996, 34 – 36.en_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


Files in this item

Name:
199700007_ftp.pdf
Size:
1.088MB
Format:
PDF
View/Open

Show simple item record

Remediation of Harmful Language

The University of Michigan Library aims to describe library materials in a way that respects the people and communities who create, use, and are represented in our collections. Report harmful or offensive language in catalog records, finding aids, or elsewhere in our collections anonymously through our metadata feedback form. More information at Remediation of Harmful Language.

Accessibility

If you are unable to use this file in its current format, please select the Contact Us link and we can modify it to make it more accessible to you.