Synthesis of Furo[2,3-f]isoquinolines by Aromatic Claisen Rearrangement and Subsequent Cyclization

Mercedes Törincsi; Pál Kolonits; Endre Pálosi; Lajos Novák

doi:10.1055/s-2006-958954

PAPER

Synthesis of Furo[2,3-f]isoquinolines by Aromatic Claisen Rearrangement and Subsequent Cyclization

Mercedes Törincsi, Pál Kolonits, Endre Pálosi, Lajos Novák*
Institute for Organic Chemistry, Budapest University of Technology and Economics, Research Group for Alkaloid Chemistry, Hungarian Academy of Sciences, Gellért tér 4, 1111 Budapest, Hungary
Fax: +36(1)4533297; e-Mail: lnovak@mail.bme.hu;

Abstract

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Abstract

Furo[2,3-f]isoquinolines were prepared by reacting isoquinolin-5-ol with an allyl bromide. Reaction between the sodium salt of isoquinolinol and and allyl bromide led to the formation of an allyloxyisoquinoline, which was thermally rearranged. The resultant allylisoquinoline was then subjected to acid-catalyzed cyclization to afford the title compound.

Key words

furo[2,3-f]isoquinoline - allyl aryl ethers - Claisen rearrangement - ring closure - sonochemical conditions

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References

<A NAME="RT11606SS-1">1</A> Yasuhiko K, Matsumoto T, and Fujii N. inventors; PCT Int. Appl. 20030103. Chem. Abstr. 2005, 138: 73247

<A NAME="RT11606SS-2">2</A> Roger R. Guillaumel J. Demerseman P. Platzer N. Buisson J.-P. Bull. Soc. Chim. Fr. 1972, 4201

For excellent monographs on the Claisen rearrangement, see:

<A NAME="RT11606SS-3A">3a</A> Tarbell DS. Org. React. 1944, 2: 2

<A NAME="RT11606SS-3B">3b</A> Ziegler FE. Acc. Chem. Res. 1977, 10: 227

<A NAME="RT11606SS-3C">3c</A> Murray AW. Org. React. Mech. 1980, 517

<A NAME="RT11606SS-3D">3d</A> Lutz RP. Chem. Rev. 1984, 84: 205

<A NAME="RT11606SS-3E">3e</A> Ziegler FE. Chem. Rev. 1988, 88: 1423

<A NAME="RT11606SS-3F">3f</A> Nubbemeyer U. Synthesis 2003, 961

<A NAME="RT11606SS-3G">3g</A> Castro AMM. Chem. Rev. 2004, 104: 2939

<A NAME="RT11606SS-4">4</A> Some ethers of isoquinolin-5-ol expressed strong bactericidal activity on Helicobacter pylori: Yoshida Y. Barrett D. Azami H. Morinaga C. Matsumoto S. Matsumoto Y. Takasugi H. Bioorg. Med. Chem. 1999, 7: 2647

In recent years there has been an increasing interest in the use of microwave irradiation to heat chemical reactions, see:

<A NAME="RT11606SS-5A">5a</A> Farand JA. Denissova I. Barriault L. Heterocycles 2004, 62: 735

<A NAME="RT11606SS-5B">5b</A> Kotha S. Mandal K. Deb AC. Banerjee S. Tetrahedron Lett. 2004, 45: 9603

<A NAME="RT11606SS-5C">5c</A> Rao VV. Reddy GV. Yadla R. Narsaiah B. Rao PS. ARKIVOC 2005, (iii): 211

<A NAME="RT11606SS-5D">5d</A> Jacob AM. Moody CJ. Tetrahedron Lett. 2005, 46: 8823

<A NAME="RT11606SS-5E">5e</A> Kremsner JM. Kappe CO. J. Org. Chem. 2006, 71: 4651 ; and references cited therein

<A NAME="RT11606SS-6">6</A> Lauer WM. Filbert WF. J. Am. Chem. Soc. 1936, 58: 1388

<A NAME="RT11606SS-7A">7a</A> Hurd CD. Pollack MA. J. Org. Chem. 1939, 3: 550

<A NAME="RT11606SS-7B">7b</A> Marwell EN. J. Org. Chem. 1960, 25: 676

<A NAME="RT11606SS-7C">7c</A> Lauer WM. Douldoras GA. Hileman RE. Lupino R. J. Org. Chem. 1961, 26: 4785

<A NAME="RT11606SS-7D">7d</A> Marwell EN. Anderson DR. Ong J. J. Org. Chem. 1962, 27: 1109

<A NAME="RT11606SS-7E">7e</A> Roberts RM. Landolt RG. Greene RN. Heyer EW. J. Am. Chem. Soc. 1967, 89: 1404

<A NAME="RT11606SS-7F">7f</A> Scheinmann F. Barner R. Schmid H. Helv. Chim. Acta 1968, 51: 1603

<A NAME="RT11606SS-7G">7g</A> Rhoads SJ. Raulins NR. Org. React. 1974, 22: 1

<A NAME="RT11606SS-7H">7h</A> Schobert R. Siegfried S. Gordon G. Mulholland D. Nieuwenhuyzen M. Tetrahedron Lett. 2001, 42: 4561

The Claisen rearrangement and subsequent cyclization under acidic conditions has been widely used for the preparation of cyclic compounds. For general reviews and selected examples, see:

<A NAME="RT11606SS-8A">8a</A> Corey EJ. Cheng X.-M. The Logic of Chemical Synthesis Wiley & Sons; New York: 1989.

<A NAME="RT11606SS-8B">8b</A> Nicolaou KC. Sorensen EJ. Classics in Total Synthesis VCH; Weinheim: 1996.

<A NAME="RT11606SS-8C">8c</A> Robinson B. Chem. Rev. 1969, 69: 227

<A NAME="RT11606SS-8D">8d</A> Rischke H. Wilcock JD. Winterfeldt E. Chem. Ber. 1973, 106: 3106

<A NAME="RT11606SS-8E">8e</A> Murray RDH. Forbes IT. Tetrahedron 1978, 34: 1411

<A NAME="RT11606SS-8F">8f</A> Mohan C. Kumar V. Mahajan MP. Tetrahedron 2004, 45: 6075

<A NAME="RT11606SS-8G">8g</A> Miyata O. Takeda N. Kimura Y. Takemoto Y. Tohnai N. Miyata M. Naito T. Tetrahedron 2006, 62: 3629

<A NAME="RT11606SS-9">9</A> Cox RA. Swallow AJ. J. Chem. Soc. 1958, 3727

<A NAME="RT11606SS-10">10</A> Dondas HA. Grigg R. Thibault S. Tetrahedron 2001, 57: 7035