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 2007(7): 1003-1014
DOI: 10.1055/s-2007-965959
DOI: 10.1055/s-2007-965959
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Pyrrolo[2,1-a]isoquinolines by a Tandem 1,5-Electrocyclisation-Oxidation Process
Further Information
Received
14 December 2006
Publication Date:
28 February 2007 (online)
Publication History
Publication Date:
28 February 2007 (online)

Abstract
A simple protocol for the convenient synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines, utilising a one-pot, sequential azomethine ylide 1,5-electrocyclisation-oxidation process is described.
Key words
alkaloids - azomethine ylides - electrocyclic reaction - cycloaddition - pyrroles
-
1a
Tanaka H.Tanaka T.Etoh H.Goto S.Terada Y. Heterocycles 1999, 51: 2759 -
1b
Dyke SF.Quessy SN. In The Alkaloids Vol. 18:Rodrigo RGA. Academic Press; New York: 1981. p.1 -
1c
Tsuda Y.Sano T. In The Alkaloids Vol. 48:Cordell GA. Academic Press; San Diego: 1996. p.249 -
2a
Andersen RJ.Faulkner DJ.Cun-heng H.Van Duyne GD.Clardy J. J. Am. Chem. Soc. 1985, 107: 5492 -
2b
Cironi P.Albericio F.Alvarez M. In Progress in Heterocyclic Chemistry Vol. 16:Gribble GW.Joule JA. Pergamon; Oxford U.K.: 2004. p.1-26 - 3
Ishibashi H.Harada S.Sato K.Ikeda M.Akai S.Tamura Y.Ahmad VU.Rahman A.Rasheed T.Rehman H. Heterocycles 1987, 26: 1251 -
4a
González-Temprano I.Sotomayor N.Lete E. Synlett 2002, 593 -
4b
Katritzky AR.Mehta S.He H.-Y. J. Org. Chem. 2001, 66: 148 ; and references cited therein -
5a
Yamaguchi T.Fukuda T.Ishibashi F.Iwao M. Tetrahedron Lett. 2006, 47: 3755 -
5b
Fujikawa N.Ohta T.Yamaguchi T.Fukuda T.Ishibashib F.Iwao M. Tetrahedron 2006, 62: 594 -
5c
Iwao M.Takeuchi T.Fujikawa N.Fukuda T.Ishibashi F. Tetrahedron Lett. 2003, 44: 4443 -
6a
Cironi P.Cuevas C.Albericioa F.Alvarez M. Tetrahedron 2004, 60: 8669 -
6b
Cironi P.Manzanares I.Albericio F.Alvarez M. Org. Lett. 2003, 2959 -
6c
Ridley CPM.Reddy VR.Rocha G.Bushman FD.Faulkner DJ. Bioorg. Med. Chem. 2002, 10: 3285 -
6d
Banwell M.Flynn B.Hockless D. J. Chem. Soc., Chem. Commun. 1997, 2259 -
6e
Poissonnet G.Theret-Bettiol M.-H.Dodd RH. J. Org. Chem. 1996, 61: 2273 -
7a
Díaz M.Guitián E.Castedo L. Synlett 2001, 1164 -
7b
Zhao B.-X.Yu Y.Eguchi S. Tetrahedron 1996, 52: 12049 - 8
Olsen CA.Parera N.Albericio F.Alvarez M. Tetrahedron Lett. 2005, 46: 2041 -
9a
Ploypradith P.Kagan RK.Ruchirawat S. J. Org. Chem. 2005, 70: 5119 -
9b
Ploypradith P.Mahidol C.Sahakitpichan P.Wongbundit S.Ruchirawat S. Angew. Chem. Int. Ed. 2004, 43: 866 -
9c
Kuo R.-Y.Wu C.-C.Chang F.-R.Yeh J.-L.Chen I.-J.Wu Y.-C. Bioorg. Med. Chem. Lett. 2003, 13: 821 -
9d
Ishibashi F.Tanabe S.Oda T.Iwao M. J. Nat. Prod. 2002, 65: 500 -
9e
Ruchirawat S.Mutarapat T. Tetrahedron Lett. 2001, 42: 1205 - 10
Fujita R.Watanabe N.Tomisawa H. Chem. Pharm. Bull. 2002, 50: 225 -
11a
Groundwater PW.Nyerges M. Adv. Heterocycl. Chem. 1999, 73: 97 -
11b
Arany A.Groundwater PW.Nyerges M. Tetrahedron Lett. 1998, 39: 3267 -
11c
Arany A.Bendell D.Groundwater PW.Garnett I.Nyerges M. J. Chem. Soc., Perkin Trans. 1 1999, 2605 -
11d
Pintér Á.Nyerges M.Virányi A.Tőke L. Tetrahedron Lett. 2003, 44: 2343 -
11e
Nyerges M.Pintér Á.Virányi A.Bitter I.Tőke L. Tetrahedron Lett. 2005, 46: 377 -
11f
Nyerges M.Pintér Á.Virányi A.Blaskó G.Tőke L. Tetrahedron 2005, 61: 8199 -
11g
Nyerges M.Virányi A.Tóth J.Blaskó G.Tőke L. Synthesis 2006, 1273 -
12a
Nyerges M.Vir& aacute;nyi A.Pintér Á.Tőke L. Tetrahedron Lett. 2003, 44: 793 -
12b
Nyerges M.Tőke L. Tetrahedron Lett. 2005, 46: 7531 -
12c
Tóth J.Dancsó A.Blaskó G.Tőke L.Groundwater PW.Nyerges M. Tetrahedron 2006, 62: 5725 -
13a
Bremmer ML.Khatri NA.Weinreb SM. J. Org. Chem. 1983, 48: 3661 -
13b
Tripathi S.Misra K.Sanghvi YS. Synth. Commun. 2005, 35: 3069 - 14
Cortes C.Romere EC.Ramirez GF. J. Heterocycl. Chem. 1994, 31: 1425 -
15a
Bende Z.Simon K.Tóth G.Tõke L.Weber L. Liebigs Ann. Chem. 1982, 924 -
15b
Bende Z.Bitter I.Tõke L.Weber L.Tóth G.Janke F. Liebigs Ann. Chem. 1982, 2146 -
15c
Bende Z.Tõke L.Weber L.Tóth G.Janke F.Csonka G. Tetrahedron 1983, 40: 369 -
15d
Fejes I.Nyerges M.Tõke L.Pak CS. Tetrahedron 2000, 56: 639 -
15e
Nyerges M.Somfai B.Tóth J.Dancsó A.Blaskó G.Tőke L. Synthesis 2005, 2039