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Synthesis 2005(19): 3346-3354
DOI: 10.1055/s-2005-918457
DOI: 10.1055/s-2005-918457
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Polysubstituted Pyrroles from Nitroso-Diels-Alder Cycloadducts
Weitere Informationen
Received
2 May 2005
Publikationsdatum:
04. November 2005 (online)
Publikationsverlauf
Publikationsdatum:
04. November 2005 (online)
Abstract
Nitroso-Diels-Alder cycloaddition of various dienes combined with a straightforward sequence including N-O bond cleavage and oxidation reaction of the resulting (Z)-γ-aminoenone (or enal) leads to polysubstituted pyrrolic units.
Key words
nitroso-Diels-Alder reactions - oxidations - pyrroles - ring closure
-
1a
Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 2001, 2491 -
1b
Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1999, 2849 -
1c
Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1998, 615 -
1d
Sundberg RJ. In Comprehensive Heterocyclic Chemistry II Vol. 2:Katritzky AR.Rees CW.Scriven EFV. Pergamon; Oxford: 1996. p.119 -
1e
Heterocyclic Chemistry
4th ed.:
Joule JA.Mills K. Blackwell Science; London: 2000. Chap. 13. -
1f
Patterson JM. Synthesis 1976, 281 -
2a
Nakamura M.Hara K.Sakata G.Nakamura E. Org. Lett. 1999, 1: 1505 -
2b
Dieter RK.Yu H. Org. Lett. 2000, 2: 2283 -
2c
Benetti S.De Risi C.Marchetti P.Pollini GP.Zanirato V. Synthesis 2002, 331 -
2d
Paulus O.Alcaraz G.Vaultier M. Eur. J. Org. Chem. 2002, 2565 -
3a
Ramanathan B.Keith AJ.Armstrong D.Odom AL. Org. Lett. 2004, 6: 2957 -
3b
Fürstner A. Synlett 1999, 1523 -
3c
Li Y.Marks TJ. J. Am. Chem. Soc. 1998, 120: 1757 -
3d
Utimoto K.Miwa H.Nozaki H. Tetrahedron Lett. 1981, 22: 4277 -
4a
Kel’in AV.Sromek AW.Gevorgyan V. J. Am. Chem. Soc. 2001, 123: 2074 -
4b
Danks T.Velo-Rego D. Tetrahedron Lett. 1994, 35: 9443 - 5
Wang S.Zhu S. Org. Lett. 2003, 5: 745 -
6a
Nagafuji P.Cushman M. J. Org. Chem. 1996, 61: 4999 -
6b
Banik BK.Samajdar S.Banik I. J. Org. Chem. 2004, 69: 213 -
7a
Braun RU.Muller TJJ. Synthesis 2004, 2391 -
7b
Bharadwaj AR.Scheidt KA. Org. Lett. 2004, 6: 2465 -
7c For a recent review, see:
Balme G. Angew. Chem. Int. Ed. 2004, 43: 6238 - 8
Tejedor D.Gonzalez-Cruz D.Garcia-Tellado F.Marrero-Tellado JJ.Rodriguez ML. J. Am. Chem. Soc. 2004, 126: 8390 - 9
Reisser M.Maas G. J. Org. Chem. 2004, 69: 4913 -
10a
Takaya H.Kojima S.Murahashi S.-I. Org. Lett. 2001, 3: 421 -
10b
Dijkstra HP.ten Have R.van Leusen AM. J. Org. Chem. 1998, 63: 5332 -
10c
van Leusen D.van Leusen AM. Org. React. 2001, 57: 417 - 11
Dhawan R.Arndtsen BA. J. Am. Chem. Soc. 2004, 126: 468 - 12
Yang C.Murray WV.Wilson LJ. Tetrahedron Lett. 2003, 44: 1783 - 13
Dieltiens N.Stevens CV.De Vos D.Allaert B.Drozdzak R.Verpoort F. Tetrahedron Lett. 2004, 45: 8995 - 14
Boger DL.Boyce CW.Labroli MA.Sehon CA.Jin Q. J. Am. Chem. Soc. 1998, 121: 54 -
15a
Vogt PF.Miller MJ. Tetrahedron 1998, 54: 1317 -
15b
Tietze LF.Kettschau G. Top. Curr. Chem. 1997, 189: 1 -
15c
Streith J.Defoin A. Synlett 1996, 189 -
15d
Weinreb SM. In Comprehensive Organic SynthesisTrost BM.Fleming I.Paquette LA. Pergamon Press; New York: 1991. p.401 -
16a
Scheiner P.Chapman OL.Lassila JD. J. Org. Chem. 1969, 34: 813 -
16b
Givens RS.Choo DJ.Merchant SN.Stitt RP.Matuszewski B. Tetrahedron Lett. 1982, 23: 1327 - 17
Ragaini F.Cenini S.Brignolli D.Gasperini M.Gallo E. J. Org. Chem. 2003, 68: 460 -
18a
Okuro K.Dang T.Khumtaveeporn K.Alper H. Tetrahedron Lett. 1996, 37: 2713 -
18b
Raigani F.Cenini S.Borsani E.Dompé M.Gallo E. Organometallics 2001, 20: 3390 - 19
McClure KF.Danishefsky SJ. J. Org. Chem. 1991, 56: 850 - 20 Ring contraction of 6-trimethylsilyloxy substituted 3,6-dihydrooxazine:
Shi G.-Q.Schlosser M. Tetrahedron 1993, 49: 1445 - 21
Kresze G.Härtner H. Justus Liebigs Ann. Chem. 1973, 650 - 22
Kefalas P.Grierson DS. Tetrahedron Lett. 1993, 34: 3555 -
23a
Kresze G.Braun H. Tetrahedron Lett. 1969, 1743 -
23b
Defoin A.Fritz H.Geffroy G.Streith J. Tetrahedron Lett. 1986, 27: 3135 -
23c
Firl J.Kresze G. Chem. Ber. 1966, 99: 3695 - 24
Calvet G.Dussaussois M.Blanchard N.Kouklovsky C. Org. Lett. 2004, 6: 2449 -
25a
Kirby GW.Sweeny JG. J. Chem. Soc., Chem. Commun. 1973, 704 -
25b
Emery T.Neilands JB. J. Am. Chem. Soc. 1960, 82: 4903 - 26
Leach AG.Houk KN. J. Org. Chem. 2001, 66: 5192 -
27a
Cicchi S.Goti A.Brandi A.Guarna A.De Sarlo F. Tetrahedron Lett. 1990, 31: 3351 -
27b
Zhang D.Süling C.Miller MJ. J. Org. Chem. 1998, 63: 885 - 28
Defoin A.Joubert M.Heuchel J.-M.Strehler C.Streith J. Synthesis 2000, 1719 - 29
Tolman V.Hanus J.Sedmera P. Collect. Czech. Chem. Commun. 1999, 64: 696 - 30
Davies HML.Matasi JJ.Hodges LM.Huby NJS.Thornley C.Kong N.Houser JH. J. Org. Chem. 1997, 62: 1095 - 31
Evidente A.Piccialli G.Sisto A.Ohba M.Honda K.Fuji T. Chem. Pharm. Bull. 1992, 40: 1937