RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2007(22): 3542-3552
DOI: 10.1055/s-2007-990861
DOI: 10.1055/s-2007-990861
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 3-Trifluoromethyl- and 3-Perfluoroalkyl-Substituted 3-Aryloxy- and 3-Heteroaryloxypropenoic Acids and of the Cyclization Products, 2-Trifluoromethyl- and 2-Perfluoroalkyl-4H-chromen-4-ones
Weitere Informationen
Received
4 June 2007
Publikationsdatum:
29. Oktober 2007 (online)
Publikationsverlauf
Publikationsdatum:
29. Oktober 2007 (online)
Abstract
We describe a novel and simple method for the regiospecific synthesis of functionalized trifluoromethyl- and perfluoroalkyl-containing 4H-chromen-4-ones via the cyclization of substituted 3-aryloxy-3-perfluoroalkylpropenoic acids. The procedures give the final products in high yields, without any need for chromatographic purification, and no side products.
Key words
aldehydes - oxidations - carboxylic acids - regioselectivity - heterocycles
-
1a
Kirsch P. Modern Fluoroorganic Chemistry Wiley-VCH; Weinheim: 2004. -
1b
Uneyama K. Organofluorine Chemistry Blackwell; Oxford: 2006. -
1c
Organofluorine Chemistry: Principles and Commercial Applications
Banks RE.Smart BE.Tatlow JC. Plenum; New York: 1994. -
2a
Gross U.Rüdiger S. In Organo-Fluorine Compounds, In Houben-Weyl Vol. E10a:Baasner B.Hagemann H.Tatlow JC. Thieme; Stuttgart: 1999. p.18-26 -
2b
Chambers RD. Fluorine in Organic Chemistry Blackwell; Oxford: 2004. - 3
Bégué J.-P.Bonnet-Delpon D. Chimie Bioorganique et Médicinale du Fluor EDP Sciences/CNRS Éditions; Le Ulis/Paris: 2005. -
4a
Smart BE. J. Fluorine Chem. 2001, 109: 3 -
4b
Ismail FM. J. Fluorine Chem. 2002, 118: 27 -
5a
Horton DA.Bourne GT.Smythe ML. Chem. Rev. 2003, 103: 893 -
5b
Malikov VM.Yuldashev MP. Chem. Nat. Compd. 2002, 38: 358 -
5c
Levai A. ARKIVOC 2003, (xiv): 14 -
6a
Harborne JB. Nat. Prod. Rep. 1999, 16: 509 -
6b
Wu JH.Wang XH.Yic YH.Leeb KH. Bioorg. Med. Chem. Lett. 2003, 13: 1813 -
6c
Yamada J.Tomita Y. Biosci., Biotechnol., Biochem. 1994, 58: 2197 - 7
Marchand LL. Biomed. Pharmacother. 2002, 56: 296 -
8a
Matsui J.Kiyokawa N.Takenouchi H.Taguchi T. Leukemia Res. 2005, 29: 573 -
8b
Lim L.-C.Kuo Y.-C.Chou C.-J. J. Nat. Prod. 2000, 63: 627 - 9
Larget R.Lockhart B.Renard P.Largeron M. Bioorg. Med. Chem. Lett. 2000, 10: 835 -
10a
Groweiss A.Cardellins JH.Boyd MR. J. Nat. Prod. 2000, 63: 1537 -
10b
De Meyer N.Haemers A.Mishra L.Pandey H.-K.Pieters LAC.Van den Berghe DA.Vlietinck AJ. J. Med. Chem. 1991, 34: 736 - 11
Nohara A.Kuriki H.Saijo T.Ukawa K.Murata T.Kanno M.Sanno Y. J. Med. Chem. 1975, 18: 34 - 12
Shivji GM.Zielinska E.Kondo S.Mukhtar H.Sander DN. J. Invest. Dermatol. 1996, 106: 609 - 13
Mori K.Audran G.Monti H. Synlett 1998, 259 -
14a
Hadjeri M.Barbier M.Ronot X.Mariotte A.-M.Boumendjel A.Boutonnat J. J. Med. Chem. 2003, 46: 2125 -
14b
Ellis GP.Barker G. Prog. Med. Chem. 1972, 9: 65 - 15
Ferrali M.Signorini C.Caciotti B.Sugherini L.Ciccoli L.Giachetti D.Comporti M. FEBS Lett. 1997, 416: 123 -
16a
Elliot AJ.Scheiber SA.Thomas C.Pardini RS. Biochem. Pharmacol. 1992, 44: 1603 -
16b
Cos P.Ying L.Calomme M.Hu JP.Cimanga K.Van Poel B.Pieters L.Vlietnck AJ.Vanden Berghe D. J. Nat. Prod. 1998, 61: 71 -
17a
Banerji A.Goomer N. Synthesis 1980, 874 -
17b
Khanna MS.Singh OV.Garg CP.Kapoor RP. J. Chem. Soc., Perkin Trans. 1 1992, 2565 -
18a
Allan J.Robinson R. J. Chem. Soc. 1924, 2192 -
18b
Rossolin V.Lokskin V.Samat A.Guglielmetti R. Tetrahedron 2003, 59: 7725 -
19a
Baker W. J. Chem. Soc. 1933, 1381 -
19b
Muller E.Kalai T.Jeko J.Hideg K. Synthesis 2000, 1415 -
19c
Ganguly AK.Kaur S.Mahata PK.Biswas D.Pramanik BN.Chan TM. Tetrahedron Lett. 2005, 46: 4119 - 20
Miao H.Yang Z. Org. Lett. 2000, 2: 1765 - 21
Zhou C.Dubrovsky AV.Larock RC. J. Org. Chem. 2006, 71: 1728 - 22
Kumar P.Bodas MS. Org. Lett. 2000, 2: 3821 -
23a
Sosnovskikh VY.Barabanov MA.Sizov AY. Russ. Chem. Bull. 2002, 51: 1280 -
23b
Sosnovskikh VY.Usachev BI. Russ. Chem. Bull. 2004, 53: 383 -
23c
Ishar MPS.Singh G.Singh S.Sreenivasan KK.Singh G. Bioorg. Med. Chem. Lett. 2006, 16: 1366 - 24
Sosnovskikh VY.Usachev BI. Russ. Chem. Bull. 2002, 51: 1954 -
25a
Prim D.Fuss A.Kirsch G.Silva AMS. J. Chem. Soc., Perkin Trans. 2 1999, 1175 -
25b
Schulze B.Kirsten G.Kirrbach S.Rahm R.Heimgarten H. Helv. Chim. Acta 1991, 74: 1059 -
25c
Clough SC.Gupton JT.Driscoll DR.Griffin KA.Hewitt AM.Hudson MS.Ligali SA.Mulcahy SP.Roberts MN.Miller RB.Belachew TT.Kamenova ID.Kanters RPF.Norwood BK. Tetrahedron 2004, 60: 10165 -
26a
Alvernhe G.Langlois B.Laurent A.Le Drean I.Selmi A.Weissenfels M. Tetrahedron Lett. 1991, 32: 643 -
26b
Kirsch G.Prim D.Leising F.Mignani G. J. Heterocycl. Chem. 1994, 31: 1005 -
26c
Tasker AS. J. Med. Chem. 1997, 40: 322 -
27a
El Kharrat S.Laurent P.Blancou H. J. Org. Chem. 2006, 71: 6742 -
27b
El Kharrat S,Laurent P, andBlancou H. inventors; PCT Patent FR2005000863. 2005; Chem. Abstr. 2005, 143, 386772 -
28a
El Kharrat S.Skander M.Dahmani A.Laurent P.Blancou H. J. Org. Chem. 2005, 70: 8327 -
28b
Laurent P.Blancou H.Commeyras A. Tetrahedron Lett. 1992, 2489 -
29a
Laurent P.Tra Ahn D.Blancou H.Commeyras A. J. Fluorine Chem. 1999, 94: 139 -
29b
Laurent P.Blancou H.Commeyras A. J. Fluorine Chem. 1993, 62: 161 - 30
El Kharrat S.Laurent P.Blancou H. J. Org. Chem. 2006, 71: 8637 -
31a
Lindgren BO.Nilsson T. Acta Chem. Scand. 1973, 27: 888 -
31b
Kudesia VP. Bull. Soc. Chim. Belg. 1972, 81: 623 - 32
Dalcanale E.Montanari F. J. Org. Chem. 1986, 51: 567 - 33
Matsubara K.Oba A.Usui Y. Magn. Reson. Chem. 1998, 36: 761 - 34
Zoghlami H.Chehidi I.Chaabouni MM.Baklouti A. J. Fluorine Chem. 2004, 125: 1887 -
35a
Kitazume T.Nagura H.Koguchi S. J. Fluorine Chem. 2004, 125: 79 -
35b
Marival-Hodebar L.Tordeux M.Wakselman C. Magn. Reson. Chem. 1999, 37: 579 -
36a
Bacilieri C.Neuenschwander M. Helv. Chim. Acta 2000, 83: 641 -
36b
Bouchy A.Rinaldi D.Rivail J.-L. Int. J. Quantum Chem. 2004, 86: 273 -
36c
Gilli P.Bertolasi V.Ferretti V.Gilli G. J. Am. Chem. Soc. 2000, 122: 10405 -
36d
Sandström J. Top. Stereochem. 1983, 14: 83 -
37a
Sung K.Lin M.-C.Huang P.-M.Zhuang B.-R.Sung R.Wu R.-R. ARKIVOC 2005, (xiii): 131 -
37b
Pigosova J.Gatial A.Milata V.Cernuchova P.Pronayova N.Liptaj T.Matejka P. J. Mol. Struct. 2005, 744-747: 315 -
38a
Kleinpeter E. J. Serb. Chem. Soc. 2006, 71: 1 -
38b
Salon J.Milata V.Gatial A.Pronayova N.Lesko J.Cernuchova P.Rappoport Z.Vo-Thanh G.Loupy A. Eur. J. Org. Chem. 2005, 4870 -
38c
Kozerski L.Kwiecien B.Kaweçki R.Urbanczyk-Lipkowaska Z.Bocian W.Bednarek E.Sitkowski J.Maurin J.Pazderski L.Hansen PE. New J. Chem. 2004, 28: 1562 -
39a
Loudon JD.Razdan RK. J. Chem. Soc. 1954, 4299 -
39b
Gilmore JC. J. Am. Chem. Soc. 1951, 73: 5879 - 40
Gore PH. In Friedel-Crafts and Related Reactions, Aromatic Ketone Synthesis Part 1, Vol. III:Olah GA. John Wiley & Sons; New York: 1964. p.97 - 41
Olah GA.Tolgyesi WS. In Friedel-Crafts and Related Reactions, Haloalkylations Part 2, Vol. II:Olah GA. John Wiley & Sons; New York: 1964. p.686 - 42
Patinkin SH.Friedman BS. In Friedel-Crafts and Related Reactions, Alkylation of Aromatics with Alkenes and Alkanes Part 1, Vol. II:Olah GA. John Wiley & Sons; New York: 1964. p.68