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 2008(6): 921-924
DOI: 10.1055/s-2008-1032195
DOI: 10.1055/s-2008-1032195
PAPER
© Georg Thieme Verlag Stuttgart · New YorkAmino-Claisen versus Oxy-Claisen Rearrangement: Regioselective Synthesis of Pyrrolocoumarin Derivatives
Weitere Informationen
Received
3 December 2007
Publikationsdatum:
28. Februar 2008 (online)
Publikationsverlauf
Publikationsdatum:
28. Februar 2008 (online)

Abstract
Pyrrolocoumarin and its derivatives have been synthesized regioselectively in excellent yields by the amino-Claisen rearrangement of 3-N-propargylaminocoumarin and 3-N-(aryloxybut-2-ynyl)aminocoumarins.
Key words
amino-Claisen rearrangement - oxy-Claisen rearrangement - [3,3]-sigmatropic rearrangement - 3-aminocoumarin - pyrrolocoumarin - 5-exo-trig
- 1a
Murray DH.Mendez J.Broun SA. The Natural Coumarins: Occurrence, Chemistry and Biochemistry Wiley; New York: 1982. - 1b
O’Kennedy R.Thornes RD. Coumarins: Biology, Applications and Mode of Action Wiley; Chichester: 1997. - 1c
Fylaktakidou KC.Hadjipavlou-Litina DJ.Litinas KE.Nicolaides DN. Curr. Pharm. Des. 2004, 10: 3813 - 1d
Zhang W.Pugh G. Tetrahedron Lett. 2001, 42: 5613 - 2
Ukawa K.Ishiguro T.Wada Y.Nohara A. Heterocycles 1986, 24: 1931 - 3
Heber D. Arch. Pharm. 1987, 320: 402 - 4
Heber D.Berghaus T. J. Heterocycl. Chem. 1994, 31: 1353 - 5a
Santana L.Uriarte E.Gonzalez-Diaz H.Zagotto G.Soto-Otero R.Mendez-Alvarez E. J. Med. Chem. 2006, 49: 1149 - 5b
Rivkin A.Adams B. Tetrahedron Lett. 2006, 47: 2395 - 5c
Yamaguchi T.Fukuda T.Ishibashi F.Iwao M. Tetrahedron Lett. 2006, 47: 3755 ; and references cited therein - 5d
Burlison JA.Neckers L.Smith AB.Maxwell A.Blagg BSJ. J. Am. Soc. Chem. 2006, 128: 15529 - 6a
Gellert M.O’Dea MH.Itoh T.Tomizawa ZI. Proc. Natl. Acad. Sci. U.S.A. 1976, 73: 4474 - 6b
Levine C.Hiasa H.Marians KJ. Biochim. Biophys. Acta. 1998, 1400: 29 - 7
Chen G.Yee DJ.Gubernator NG.Sames D. J. Am. Chem. Soc. 2005, 127: 4544 - 8
Majumdar KC.Chattopadhyay B.Taher A. Synthesis 2007, 3647 - 9a
Majumdar KC.Muhuri S.Rahaman H.Islam R.Roy B. Chem. Lett. 2006, 35: 1430 - 9b
Majumdar KC.Rahaman H.Roy B. Lett. Org. Chem. 2006, 3: 526 - 9c
Majumdar KC.Chattopadhyay B. Synth. Commun. 2006, 36: 3125 - 9d
Majumdar KC.Mukhopadhyay PP.Basu PK. Synth. Commun. 2005, 35: 1291 - 9e
Majumdar KC.Chattopadhyay SK. Tetrahedron Lett. 2004, 45: 6871 - 9f
Majumdar KC.Bhattacharyya T. Tetrahedron Lett. 2001, 42: 4231 - 10a
Majumdar KC.Thyagrajan BS. Int. J. Sulfur Chem. 1972, 2A: 93 - 10b
Thyagrajan BS.Majumdar KC. J. Heterocyl. Chem. 1973, 12: 43 - 11a
Gazith M.Noys RM. J. Am. Chem. Soc. 1955, 77: 6091 - 11b
Gardner IJ.Noyes RM. J. Am. Chem. Soc. 1961, 83: 2409 - 12
Marcinkiewcz S.Green J.Mamalis P. Tetrahedron 1961, 14: 208 - 13a
Zsindely J.Schmidt H. Helv. Chim. Acta 1968, 51: 1510 - 13b
Majumdar KC.Thyagrajan BS.Balasubramanian KK. J. Heterocyl. Chem. 1973, 10: 159 - 14
Scheurer VH.Zsindely J.Schmidt H. Helv. Chim. Acta. 1973, 56: 478 - 15
Majumdar KC.Jana NK. Synth. Commun. 2001, 30: 4183