Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2011(11): 1691-1704
DOI: 10.1055/s-0030-1260415
DOI: 10.1055/s-0030-1260415
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New YorkPyrroles and Indolizidines from Deprotonated α-(Alkylideneamino)nitriles
Further Information
Received
10 March 2011
Publication Date:
29 April 2011 (online)
Publication History
Publication Date:
29 April 2011 (online)
Abstract
Their ready availability from simple starting materials in only two synthetic steps and their versatility as building blocks for the construction of highly substituted amines and N-heterocycles renders α-(alkylideneamino)nitriles useful synthetic intermediates. Herein, short syntheses of tri- and tetrasubstituted pyrroles including the northern half of the HMG-CoA reductase inhibitor atorvastatin as well as an access to 3-substituted indolizidines will be described.
Key words
heterocycles - carbanions - pyrroles - Umpolung - Michael addition
- 1
Seebach D.Enders D. Angew. Chem. 1975, 87: 1 - 2
Albright JD. Tetrahedron 1983, 39: 3207 - 3
Enders D.Shilvock JP. Chem. Soc. Rev. 2000, 29: 359 - 4
Opatz T. Synthesis 2009, 1941 - 5
Meyer N.Opatz T. Synlett 2003, 1427 - 6
von Miller W.Plöchl J. Ber. Dtsch. Chem. Ges. 1898, 31: 2718 - 7
Werner F.Blank N.Opatz T. Eur. J. Org. Chem. 2007, 3911 - 8
Meyer N.Werner F.Opatz T. Synthesis 2005, 945 - 9
Kison C.Meyer N.Opatz T. Angew. Chem. Int. Ed. 2005, 44: 5662 - 10
Kison C.Opatz T. Eur. J. Org. Chem. 2008, 2740 - 11
Bergner I.Opatz T. Synthesis 2007, 918 - 12
Bruylants P. Bull. Soc. Chim. Belg. 1924, 33: 467 - 13
Tsuge O.Ueno K.Kanemasa S.Yorozu K. Bull. Chem. Soc. Jpn. 1986, 59: 1809 - 14
Tsuge O.Kanemasa S.Yamada T.Matsuda K. J. Org. Chem. 1987, 52: 2523 - 15
Tsuge O.Ueno K.Kanemasa S.Yorozu K. Bull. Chem. Soc. Jpn. 1987, 60: 3347 - 16
Meyer N.Opatz T. Synlett 2004, 787 - 17
Bergner I.Opatz T. Synthesis 2007, 918 - 18
Bergner I.Opatz T. J. Org. Chem. 2007, 72: 7083 - 19
Estevez V.Villacampa M.Menendez JC. Chem. Soc. Rev. 2010, 39: 4402 - 20
Joshi U.Pipelier M.Naud S.Dubreuil D. Curr. Org. Chem. 2005, 9: 261 - 21
St. Cyr DJ.Martin N.Arndtsen BA. Org. Lett. 2007, 9: 449 - 22
Milgram BC.Eskildsen K.Richter SM.Scheidt WR.Scheidt KA. J. Org. Chem. 2007, 72: 3941 - 23
Agarwal S.Knölker H.-J. Org. Biomol. Chem. 2004, 2: 3060 - 24
Balme G. Angew. Chem. Int. Ed. 2004, 43: 6238 - 25
Trofimov BA.Mikhaleva AI.Schmidt EY.Sobenina LN. Adv. Heterocycl. Chem. 2010, 99: 209 - 26
Russel JS.Pelkey ET.Yoon-Miller SJP. Prog. Heterocycl. Chem. 2009, 21: 145 - 27
Russel JS.Pelkey ET. Prog. Heterocycl. Chem. 2009, 20: 122 - 28
Tsuge O.Ueno K. Heterocycles 1982, 19: 1411 - 29
Roth BD. inventors; EP 0409281. (Warner-Lambert Co., USA)Reference Ris Wihthout Link - 30
Pandey PS.Srinivasa Rao T. Bioorg. Med. Chem. Lett. 2004, 14: 129 - 31
Tsuge O.Kanemasa S.Yorozu K.Ueno K. Bull. Chem. Soc. Jpn. 1987, 60: 3359 - 32
Kanemasa S.Tsuge O. Adv. Cycloaddit. 1993, 3: 99 - 33
Pearson WH.Stoy P. Synlett 2003, 903 - 34
Vivanco S.Lecea B.Arrieta A.Prieto P.Morao I.Linden A.Cossio FP. J. Am. Chem. Soc. 2000, 122: 6078 - 35
Bergner I. Dissertation University of Hamburg; Germany: 2009. - 36
van der Werf A.Kellogg RM. Tetrahedron Lett. 1991, 32: 3727 - 37
Tasheva D.Petrova A.Simova S. Synth. Commun. 2007, 37: 3971 - 38
Bergner I.Wiebe C.Meyer N.Opatz T. J. Org. Chem. 2009, 74: 8243 - 39
Girard A.Sandulesco G. Helv. Chim. Acta 1936, 19: 1095 - 40
Pillot JP.Dumogues J.Calas R. C. R. Acad. Sci., Ser. C 1974, 278: 789 - 41
Gottlieb HE.Kotlyar V.Nudelman A. J. Org. Chem. 1997, 62: 7512 - 42
Lagriffoul P.-H.Tadros Z.Taillades J.Commeyras A. J. Chem. Soc., Perkin Trans. 2 1992, 1279 - 43
Kurtz P.Disselnkoetter H. Justus Liebigs Ann. Chem. 1972, 764: 69 - 44
Wright SW.Petraitis JJ.Freimark B.Giannaras JV.Pratta MA.Sherk SR.Williams JM.Magolda RL.Arner EC. Bioorg. Med. Chem. 1996, 4: 851 - 45
Weinstock HH.Fuson RC. J. Am. Chem. Soc. 1934, 56: 1241 - 46
Collman JP.Brauman JI.Doxsee KM.Halbert TR.Bunnenberg E.Linder RE.LaMar GN.Del Gaudio J.Lang G.Spartalian K. J. Am. Chem. Soc. 1980, 102: 4182 - 47
Bajgrowicz JA.El Hallaoui A.Jacquier R.Pigiere C.Viallefont P. Tetrahedron 1985, 41: 1833 - 48
Andersen SH.Sharma KK.Torssell KBG. Tetrahedron 1983, 39: 2241