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 2006(16): 2707-2718
DOI: 10.1055/s-2006-942508
DOI: 10.1055/s-2006-942508
PAPER
© Georg Thieme Verlag Stuttgart · New York
3-(Polyhaloacyl)chromones and their Hetero Analogues: Synthesis and Reactions with Amines
Weitere Informationen
Received
20 April 2006
Publikationsdatum:
19. Juli 2006 (online)
Publikationsverlauf
Publikationsdatum:
19. Juli 2006 (online)
Abstract
2-Hydroxy-2-(polyhaloalkyl)chroman-4-ones react with diethoxymethyl acetate at 140-150 °C for 15 minutes to give 3-(polyhaloacyl)chromones in good yields. The reactions of these compounds with amines proceeds at C-2 with pyrone ring-opening and formation of 2-(alkyl/arylaminomethylene)-2-hydroxy-2-(polyfluoroalkyl)chroman-4-ones.
Key words
chroman-4-ones - diethoxymethyl acetate - formylation - 3-(polyhaloacyl)chromones - amines
-
1a
Ghosh CK. J. Heterocycl. Chem. 1983, 20: 1437 -
1b
Sabitha G. Aldrichimica Acta 1996, 29: 15 - 2
Eiden F.Haverland H. Arch. Pharm. (Weinheim, Ger.) 1967, 300: 806 - 3
Széll T.Eiden F. Arch. Pharm. (Weinheim, Ger.) 1972, 305: 81 -
4a
Becket GJP.Ellis GP. Tetrahedron Lett. 1976, 719 -
4b
Ghosh CK.Bhattacharya A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1984, 23: 668 -
5a
Nohara A.Umetani T.Sanno Y. Tetrahedron Lett. 1973, 1995 -
5b
Nohara A.Umetani T.Sanno Y. Tetrahedron 1974, 30: 3553 - 6
Yokoe I.Maruyama K.Sugita Y.Harashida T.Shirataki Y. Chem. Pharm. Bull. 1994, 42: 1697 -
7a
Borrell JI.Teixidó J.Schuler E.Michelotti E. Tetrahedron Lett. 2001, 42: 5331 -
7b
Gadhwal S.Sandhu JS. J. Chem. Soc., Perkin Trans. 1 2000, 2827 -
7c
Bandyopadhyay C.Sur KR.Patra R.Sen A. Tetrahedron 2000, 56: 3583 -
7d
Sandulache A.Silva AMS.Cavaleiro JAS. Tetrahedron 2002, 58: 105 -
7e
Singh G.Singh G.Ishar MPS. Synlett 2003, 256 -
7f
Singh G.Singh L.Ishar MPS. Tetrahedron 2002, 58: 7883 -
7g
Kaye PT.Nchinda AT.Sabbagh LV.Bacsa J. J. Chem. Res., Synop. 2003, 111 -
7h
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Tolmachev AA. Synlett 2004, 2287 -
7i
Kumar K.Kapoor R.Ishar MPS. Org. Lett. 2000, 2: 2023 -
7j
Ghosh T.Bandyopadhyay C. Tetrahedron Lett. 2004, 45: 6169 -
7k
Quiroga J.Rengifo A.Insuasty B.Abonía R.Nogueras M.Sánchez A. Tetrahedron Lett. 2002, 43: 9061 -
7l
Lacova M.Loos D.Furdik M.Matulova M.El-Shaaer HM. Molecules 1998, 3: 149 -
8a
Welch JT. Tetrahedron 1987, 43: 3123 -
8b
McClinton MA.McClinton DA. Tetrahedron 1992, 48: 6555 -
8c
Lin P.Jiang J. Tetrahedron 2000, 56: 3635 -
8d
Burton DJ.Yang Z.-Y. Tetrahedron 1992, 48: 189 -
9a
Sosnovskikh VYa.Usachev BI. Russ. Chem. Bull. 2001, 50: 1426 -
9b
Sosnovskikh VYa.Vorontsov II.Kutsenko VA. Russ. Chem. Bull. 2001, 50: 1430 -
9c
Sosnovskikh VYa.Kutsenko VA.Yachevskii DS. Mendeleev Commun. 1999, 204 -
9d
Sosnovskikh VYa.Usachev BI.Sizov AYu.Barabanov MA. Synthesis 2004, 942 -
10a
Sosnovskikh VYa.Usachev BI.Sevenard DV.Röschenthaler G.-V. Tetrahedron 2003, 59: 2625 -
10b
Sosnovskikh VYa.Usachev BI.Vorontsov II. Tetrahedron 2003, 59: 2549 -
10c
Sosnovskikh VYa.Barabanov MA.Usachev BI. Org. Lett. 2003, 5: 2501 -
10d
Sosnovskikh VYa.Barabanov MA.Usachev BI. J. Org. Chem. 2004, 69: 8297 -
10e
Sosnovskikh VYa.Usachev BI.Vorontsov II. J. Org. Chem. 2002, 67: 6738 -
11a
Sosnovskikh VYa.Sevenard DV.Usachev BI.Röschenthaler G.-V. Tetrahedron Lett. 2003, 44: 2097 -
11b
Sosnovskikh VYa.Usachev BI.Sevenard DV.Röschenthaler G.-V. J. Org. Chem. 2003, 68: 7747 -
11c
Sosnovskikh VYa.Usachev BI. Synthesis 2002, 2341 -
11d
Sosnovskikh VYa.Usachev BI.Sizov AYu.Vorontsov II.Shklyaev YuV. Org. Lett. 2003, 5: 3123 -
11e
Sosnovskikh VYa.Usachev BI.Sizov AYu. Synlett 2004, 1765 -
11f
Sosnovskikh VYa.Usachev BI.Sizov AYu.Kodess MI. Tetrahedron Lett. 2004, 45: 7351 -
12a
Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications
Filler R.Kobayashi Y.Yagupolskii LM. Elsevier; Amsterdam: 1993. -
12b
Welch JT.Eswarakrishnan S. Fluorine in Bioorganic Chemistry Wiley; New York: 1991. -
12c
Hiyama T. Organofluorine Compounds. Chemistry and Application Springer-Verlag; Berlin: 2000. - 13
Sosnovskikh VYa.Irgashev RA. Synlett 2005, 1164 - 14
Gelin S.Chantegrel B.Nadi AI. J. Org. Chem. 1983, 48: 4078 -
15a
Montgomery JA.Holum LB. J. Am. Chem. Soc. 1958, 80: 404 -
15b
Montgomery JA.Temple C. J. Am. Chem. Soc. 1958, 80: 409 -
15c
Cushman M.Mavandadi F.Kugelbrey K.Bacher A. Bioorg. Med. Chem. 1998, 6: 409 -
15d
Akahoshi F.Takeda S.Okada T.Kajii M.Nishimura H.Sugiura M.Inoue Y.Fukaya C.Naito Y.Imagawa T.Nakamura N. J. Med. Chem. 1998, 41: 2985 -
16a
Morera E.Ortar G. Tetrahedron Lett. 1981, 22: 1273 -
16b
Sosnovskikh VYa.Sizov AYu.Usachev BI. Russ. Chem. Bull. 2002, 51: 1270 - 17
Sosnovskikh VYa.Usachev BI. Synthesis 2002, 1007 - 18a Morita Y., Kamakura R., Takeda M., Yamamoto Y.; J. Chem. Soc., Chem. Commun.; 1997, 359
-
18b
Sosnovskikh VYa.Usachev BI.Sizov AYu. Russ. Chem. Bull. 2002, 51: 2109 -
18c
Sosnovskikh VYa.Usachev BI.Bogdanov EA. Russ. Chem. Bull. 2001, 50: 568 -
19a
Daia GE.Gabbutt CD.Hepworth JD.Heron BM.Hibbs DE.Hursthouse MB. Tetrahedron Lett. 1998, 39: 1215 -
19b
Tochtermann W.Frey G.Klein HA. Liebigs Ann. Chem. 1977, 2018 -
19c
Ghosh CK.Bandyopadhyay C.Tewari N. J. Org. Chem. 1984, 49: 2812 - 20
Sosnovskikh VYa.Barabanov MA. J. Fluorine Chem. 2003, 120: 25 - 21
Ellis GP. Chromenes, Chromanones and Chromones. In The Chemistry of Heterocyclic Compounds Vol. 31: Wiley; New York: 1977. - 22
Sosnovskikh VYa. Russ. Chem. Rev. 2003, 72: 489 - 23
Kostka K. Roczniki Chem. 1966, 40: 1683 ; Chem. Abstr. 1967, 66, 94776v - 24
Fitton AO.Frost JR.Houghton PG.Suschitzky H. J. Chem. Soc., Perkin Trans. 1 1979, 1691 - 25
Stankovicova H.Lacova M.Gaplovsky A.Chovancova J.Pronayova N. Tetrahedron 2001, 57: 3455 - 26
Sosnovskikh VYa.Usachev BI. Russ. Chem. Bull. 2001, 50: 453 - 27
Jensen BS. Acta Chem. Scand. 1959, 13: 1668