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Synthesis 2010(19): 3274-3281
DOI: 10.1055/s-0030-1258189
DOI: 10.1055/s-0030-1258189
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Expeditious Synthesis of Trifluoromethylated Heterocycles: Noncatalytic 1,3-Dipolar Cyclization of Azomethine Imines with (α-Trifluoromethyl)acrylates
Further Information
Received
7 May 2010
Publication Date:
09 August 2010 (online)
Publication History
Publication Date:
09 August 2010 (online)
Abstract
A convenient, simple, and expeditious procedure for the preparation of novel trifluoromethylated bicyclic pyrazolidinone systems by noncatalytic 1,3-dipolar cyclization of azomethine imines with tert-butyl 2-(trifluoromethyl)prop-2-enoate is presented.
Key words
bicyclic compounds - fluorine - cycloadditions - heterocycles - imines - drugs
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Bioactive Heterocycles I
Eguchi S. Springer; Heidelberg: 2006. -
1b
Joule JA.Mills K. Heterocyclic Chemistry at a Glance Blackwell; Oxford: 2007. -
1c
Georgii GF. In Advances in Heterocyclic Chemistry Vol. 86:Katritzky AR. Elsevier; Amsterdam: 2004. p.129 -
2a
Kirk K. J. Fluorine Chem. 2006, 127: 1013 -
2b
Ismail FMD. J. Fluorine Chem. 2002, 118: 27 -
2c
Fluorine
in Medicinal Chemistry and Chemical Biology
Ojima I. Blackwell; Oxford: 2009. -
2d
Purser S.Moore PR.Swallow S.Gouverneur V. Chem. Soc. Rev. 2008, 37: 320 -
2e
Isanbor C.O’Hagan D. J. Fluorine Chem. 2006, 127: 303 -
2f
Bégué J.-P.Bonnet-D D. J. Fluorine Chem. 2006, 127: 992 -
3a
Andrei AG.Kirk LK. Fluorinated Heterocycles, In Fluorinated Heterocycles, ACS Symposium Series 1003Andrei AG.Kirk LK. American Chemical Society; Washington DC: 2009. Chap. 1. p.3-20 -
3b
Harper DB.O’Hagan D. Nat. Prod. Rep. 1994, 11: 123 -
3c
O’Hagan D.Harper DB. J. Fluorine Chem. 1999, 100: 127 -
3d
Muzalevskiy VM.Nenajdenko VG.Shastin AV.Balenkova ES.Haufe G. Synthesis 2009, 2249 -
4a
Shibata N.Furukawa T.Reddy DS. Chim. Oggi 2009, 27: 38 -
4b
Shibata N.Mizuta S.Kawai H. Tetrahedron: Asymmetry 2008, 19: 2633 -
4c
Shibata N.Ishimaru T.Nakamura S.Toru T. J. Fluorine Chem. 2007, 128: 469 -
4d
Shibata N. J. Synth. Org. Chem. Jpn. 2006, 64: 14 -
5a
Kirsch P. Modern Fluoroorganic Chemistry Wiley-VCH; Weinheim: 2004. -
5b
Organofluorine
Compounds in Medicinal Chemistry and Biomedical Applications
Filler R.Kobayashi Y.Yagupolskii LM. Elsevier; Amsterdam: 1993. -
6a
Percy JM. Top. Curr. Chem. 1997, 193: 131 -
6b
Konev AS.Khlebnikov AF. Collect. Czech. Chem. Commun. 2008, 73: 1553 -
7a
Skarpos H.Röschenthaler G.-V. Chim. Oggi 2008, 76: 7 -
7b
Shibata N.Fujimoto H.Mizuta S.Ogawa S.Ishiuchi Y.Nakamura S.Toru T. Synlett 2006, 3484 - 8
Eguchi H.Nishiyama S.Ishikawa S. TOSOH Res. Technol. Rev. 2003, 47: 85 ; Chem. Abstr. 2004, 141, 227160 -
9a
Avenoza A.Busto JH.Jimènez-Osés G.Peregrina JM. J. Org. Chem. 2005, 70: 5721 -
9b
Salaheldin AM.Yi Z.Kitazume T. J. Fluorine Chem. 2004, 125: 1105 -
9c
Colantoni D.Fioravanti S.Pellacani L.Tardella PA. Org. Lett. 2004, 6: 197 -
9d
Matteis VD.Delft FLV.Gelder RD.Tiebes J.Rutjes FPJT. Tetrahedron Lett. 2004, 45: 959 -
9e
Iseki K.Kuroki Y.Nagai T.Kobayashi Y. Chem. Pharm. Bull. 1996, 44: 477 -
9f
Iseki K.Kuroki Y.Nagai T.Kobayashi Y. J. Fluorine Chem. 1994, 69: 5 -
9g
Hanzawa Y.Suzuki M.Kobayashi Y.Taguchi T.Iitaka Y. J. Org. Chem. 1991, 56: 1718 -
9h
Yamazaki T.Ohnogi T.Kitazume T. Tetrahedron: Asymmetry 1990, 1: 215 -
9i
Hanzawa Y.Suzuki M.Kobayashi Y. Tetrahedron Lett. 1989, 30: 571 -
9j
Kitazume T.Murata K.Kokusho Y.Iwasaki S.
J. Fluorine Chem. 1988, 39: 75 -
9k
Fuchikami T.Shibata Y.Suzuki Y. Tetrahedron Lett. 1986, 27: 3173 -
9l
Yamazaki T.Hiraoka S.Kitazume T. J. Org. Chem. 1994, 59: 5100 - 10
Ogawa S.Yasui H.Tokunaga E.Nakamura S.Shibata N. Chem. Lett. 2009, 38: 1006 -
11a
Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry
Toward Heterocycles and Natural Products
Padwa A.Pearson WH. Wiley; New York: 2003. -
11b
1,3-Dipolar
Cycloaddition Chemistry
Vols.1-2:
Padwa A. Wiley; New York: 1984. -
11c
Carmen N.Jose MS. Top. Heterocycl. Chem. 2008, 12: 117 -
12a
Huisgen R.Weinberger R. Tetrahedron Lett. 1985, 26: 5119 -
12b
Dorn H. Tetrahedron Lett. 1985, 26: 5123 -
12c
Dorn H.Kreher T. Heterocycles 1994, 38: 2171 -
12d
Svete J.Preseren A.Stanovnik B.Golic L.Golic-Grdadolnik S. J. Heterocycl. Chem. 1997, 34: 1323 -
12e
Chuang T.-H.Sharpless KB. Helv. Chim. Acta. 2000, 83: 1734 -
12f
Pezdirc L.Jovanovski V.Bevk D.Jakše R.Pirc S.Meden A.Stanovnik B.Svete J. Tetrahedron 2005, 61: 3977 -
12g
Chen W.Yuan X.-H.Li R.Du W.Wu Y.Ding L.-S.Chen Y.-C. Adv. Synth. Catal. 2006, 348: 1818 -
12h
Pezdirc L.Cerkovnik J.Pirc S.Stanovnik B.Svete J. Tetrahedron 2007, 63: 991 -
12i
Suga H.Funyu A.Kakehi A. Org. Lett. 2007, 9: 97 -
12j
Pezdirc L.Bevk D.Grošelj U.Meden A.Stanovnik B.Svete J. J. Comb. Chem. 2007, 9: 717 -
12k
Chen W.Du W.Duan Y.-Z.Wu Y.Yang S.-Y.Chen Y.-C. Angew. Chem. Int. Ed. 2007, 46: 7667 -
12l
Kato T.Fujinami S.Ukaji Y.Inomata K. Chem. Lett. 2008, 37: 342 -
12m
Sibi MP.Rane D.Stanley LM.Soeta T. Org. Lett. 2008, 10: 2971 -
12n
Pezdirc L.Stanovnik B.Svete J. Collect. Czech. Chem. Commun. 2009, 74: 835 -
12o
Yamashita Y.Kobayashi S. Chem. Lett. 2009, 38: 678 - 13
Hanessian S.McNaughton-Smith G.Lombart H.-G.Lubell WD. Tetrahedron 1997, 53: 12789 ; and references cited therein