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
Synthesis 2006(15): 2568-2572
DOI: 10.1055/s-2006-942461
DOI: 10.1055/s-2006-942461
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Convenient Synthesis of 3-Pyridinyl- and 3-Pyrimidinylcoumarins
Further Information
Received
13 March 2006
Publication Date:
04 July 2006 (online)
Publication History
Publication Date:
04 July 2006 (online)
Abstract
A mild and efficient synthesis of 3-pyridinyl- and 3-pyrimidinylcoumarins through one-pot tandem condensation-cyclization of various 2′-hydroxyacetophenones and pyridinyl- or pyrimidinylacetic acids is described.
Key words
coumarin - benzopyran - Perkin reaction - DCC coupling - SERM
-
1a
Kanojia RM.Jain N.Xu J.Sui Z. Tetrahedron Lett. 2004, 45: 5837 -
1b
Kanojia RM,Jain N,Ng R,Sui Z, andXu J. inventors; Patent WO 2003053977. ; Chem. Abstr. 2003, 139, 85328 -
2a
Perkin WH. J. Chem. Soc. 1868, 21: 53 -
2b
Johnson JR. Org. React. 1942, 1: 210 -
2c
Vijayan KK. Indian J. Heterocycl. Chem. 1998, 8: 1 -
2d
Mahling JA.Schmidt RR. Liebigs Ann. Chem. 1995, 467 -
3a
Kakehi A.Ito S.Suga H.Yasuraoka K. Heterocycles 2001, 54: 185 -
3b
Brufola G.Fringuelli F.Piermatti O.Pizzo F. Heterocycles 1997, 45: 1715 -
3c
Bojilova A.Nikolova R.Ivanov C.Rodios NA.Terzis A.Raptopoulou CP. Tetrahedron 1996, 52: 12597 -
4a
Sethna S.Phadke R. Org. React. 1953, 7: 1 -
4b
Baran-Marszak M.Massicot J.Molho D. Bull. Soc. Chim. Fr. 1971, 191 -
4c
Wang LM.Xia JJ.Tian H.Qian CT.Ma Y. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2003, 42: 2097 -
4d
Bose DS.Rudradas AP.Babu MH. Tetrahedron Lett. 2002, 43: 9195 -
5a
Rayabarapu DK.Sambaiah T.Cheng C.-H. Angew. Chem. Int. Ed. 2001, 40: 1286 -
5b
Yoneda E.Sugioka T.Hirao K.Zhang S.-W.Takahashi S. J. Chem. Soc., Perkin Trans. 1 1998, 477 -
5c
Van T N.Debenedetti S.De Kimpe N. Tetrahedron Lett. 2003, 44: 4199 -
5d
Trost BM.Toste FD. J. Am. Chem. Soc. 1996, 108: 6305 -
5e
Kadnikov DV.Larock RC. J. Org. Chem. 2003, 68: 9432 -
5f
Catellani M.Chuisoli GP.Fagnola MC.Solari G. Tetrahedron Lett. 1994, 35: 5919 -
5g
Catellani M.Chuisoli GP.Fagnola MC.Solari G. Tetrahedron Lett. 1994, 35: 5923 -
5h
Jia C.Piao D.Oyamada J.Lu W.Kitamura T.Fujiwara Y. J. Org. Chem. 2000, 65: 7516 -
5i
Park KH.Jung G.Chung YK. Synlett 2004, 2541 -
6a
Bhagwat SS,McKie JA, andKhammungkhune S. inventors; Patent WO 2001049673. ; Chem. Abstr. 2001, 135, 92545 -
6b
Stein BM,Anderson DW,Gayo LM,Sutherland MS,Doubleday M,Shevlin GI,Kois A,Khammungkhune S,Jalluri RK,Bhagwat SS, andMcKie JA. inventors; Patent WO 2000039120. ; Chem. Abstr. 2000, 133, 73934 -
6c
Wolfbeis OS.Marhold H. Chem. Ber. 1985, 118: 3664 -
6d
Schiedel M.-S.Briehn CA.Bauerle P. Angew. Chem. Int. Ed. 2001, 40: 4677 -
7a
Daisley RW.Hanbali JR. Synth. Commun. 1981, 11: 743 -
7b
Hennessy EJ.Buchwald SL. Org. Lett. 2002, 4: 269 - 8
Moffett RB. J. Med. Chem. 1964, 7: 446 -
9a
Lokhande PD.Ghiya BJ. J. Indian Chem. Soc. 1989, 66: 314 -
9b
Rao PP.Srimannarayana G. Synthesis 1981, 887 -
9c
Rao-Subha AV.Sabitha G. Synth. Commun. 1987, 17: 341 -
9d
Ming Y.Boykin DW. Heterocycles 1987, 26: 3229 -
9e
Gallastegui DJ.Lago JM.Palomo C. J. Chem. Res., Synop. 1984, 17 -
9f
McKie JA.Bhagwat SS.Brady H.Doubleday M.Gayo L.Hickman M.Jalluri RK.Khammungkhune S.Kois A.Mortensen D.Richard N.Sapienza J.Shevlin G.Stein B. Bioorg. Med. Chem. Lett. 2004, 14: 3407 - 10
Romano JJ.Casillas E. Tetrahedron Lett. 2005, 46: 2323