E/Z-Selective Synthesis of Alkylidene-3-oxo-3H-isobenzofurans by Reaction of Silyl
Enol Ethers with Phthaloyl Dichloride

Satenik Mkrtchyan; Zorik Chilingaryan; Gagik Ghazaryan; Rüdiger Dede; Nasir Rasool; Muhammad A. Rashid; Alexander Villinger; Helmar Görls; Gnuni Karapetyan; Tariel V. Ghochikyan; Ashot Saghiyan; Peter Langer

doi:10.1055/s-0030-1260071

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

Teilen / Bookmarken

Facebook Linkedin Weibo

PDF herunterladen

Synthesis 2011(14): 2281-2290
DOI: 10.1055/s-0030-1260071

PAPER

E/Z-Selective Synthesis of Alkylidene-3-oxo-3H-isobenzofurans by Reaction of Silyl Enol Ethers with Phthaloyl Dichloride

Satenik Mkrtchyan^a, Zorik Chilingaryan^a,b, Gagik Ghazaryan^a,b, Rüdiger Dede^a, Nasir Rasool^a,c, Muhammad A. Rashid^a, Alexander Villinger^a, Helmar Görls^d, Gnuni Karapetyan^a, Tariel V. Ghochikyan^b, Ashot Saghiyan^b,e, Peter Langer*^a,f
^a Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany
^b Faculty of Chemistry, Yerevan State University, Alex Manoogian 1, 0025 Yerevan, Armenia
^c Government College University, Faisalabad, Punjab, Pakistan
^d Institut für Anorganische und Analytische Chemie, Universität Jena, August-Bebel-Str. 2, 07740 Jena, Germany
^e CJSC Scientific Research Institute of Biotechnology, Gyurjyan Str. 14, 0056, Yerevan, Armenia
^f Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;

Weitere Informationen

Publikationsverlauf

Received 22 March 2011
Publikationsdatum:
15. Juni 2011 (online)

Abstract
Volltext
Referenzen

Artikel einzeln kaufen Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

The reaction of silyl enol ethers with phthaloyl dichloride afforded alkylidene-3-oxo-3H-isobenzofurans with very good E/Z-selectivity.

Key Words

cyclizations - O-heterocycles - phthalic acid derivatives - silyl enol ethers

References

For reviews, see for example:
1a Rao YS. Chem. Rev. 1976, 76: 625

Suche in Google Scholar
1b Pattenden G. Prog. Chem. Nat. Prod. 1978, 35: 133

Suche in Google Scholar
1c Gill M. Steglich W. Prog. Chem. Org. Nat. Prod. 1987, 51: 1

Suche in Google Scholar
1d Knight DW. Contemp. Org. Synth. 1994, 1: 287

Suche in Google Scholar
1e Negishi E.-i. Kotora M. Tetrahedron 1997, 53: 6707

Suche in Google Scholar
For reviews of syntheses of γ-alkylidenebutenolides, see:
1f Brückner R. Chem. Commun. 2001, 141
1g Brückner R. Curr. Org. Chem. 2001, 5: 679

Suche in Google Scholar
2a Rossi R. Bellina F. Biagetti M. Mannina L. Tetrahedron Lett. 1998, 39: 7799

Suche in Google Scholar
2b Xu C. Negishi E.-i. Tetrahedron Lett. 1999, 40: 431

Suche in Google Scholar
3a Siegel K. Brückner R. Chem. Eur. J. 1998, 4: 1116

Suche in Google Scholar
3b Görth FC. Brückner R. Synthesis 1999, 1520
4a Goerth F. Umland A. Brückner R. Eur. J. Org. Chem. 1998, 1055
4b v. d. Ohe F. Brückner R. Tetrahedron Lett. 1998, 39: 1909

Suche in Google Scholar
4c Hanisch I. Brückner R. Synlett 2000, 374
5a Ingham CF. Massy-Westropp RA. Reynolds GD. Thorpe WD. Aust. J. Chem. 1975, 28: 2499

Suche in Google Scholar
5b Knight DW. Pattenden G. J. Chem. Soc., Perkin Trans. 1 1979, 62
6 Albrecht U. Nguyen VTH. Langer P. Synthesis 2006, 1111

Thieme Connect
7 For a review of 1,3-bis(silyl enol ethers), see: Langer P. Synthesis 2002, 441
8 For a review of cyclizations of 1,3-bis(silyl enol ethers) with oxalyl chloride, see: Langer P. Synlett 2006, 3369

Thieme Connect
9a Naito T. Katsuhara T. Niitsu K. Ikeya Y. Okada M. Mitsuhashi H. Phytochemistry 1992, 31: 639

Suche in Google Scholar
9b Hagemaier J. Batz O. Schmidt J. Wray V. Hahlbrock K. Strack D. Phytochemistry 1999, 51: 629

Suche in Google Scholar
9c Pushan W. Xuanliang G. Yixiong W. Fukuyama Y. Miura I. Sugawara M. Phytochemistry 1984, 23: 2033

Suche in Google Scholar
9d Bellina F. Ciucci D. Vergamini P. Rossi R. Tetrahedron 2000, 56: 2533

Suche in Google Scholar
9e Li S. Wang Z. Fang X. Yang Y. Li Y. Synth. Commun. 1997, 27: 1783

Suche in Google Scholar
9f Kobayashi M. Mitsuhashi H. Chem. Pharm. Bull. 1987, 35: 4789

Suche in Google Scholar
9g Kobayashi M. Fujita M. Mitsuhashi H. Chem. Pharm. Bull. 1987, 35: 1427

Suche in Google Scholar
10a Yoshikawa M. Uchida E. Chatani N. Murakami N. Yamahara J. Chem. Pharm. Bull. 1992, 40: 3121

Suche in Google Scholar
10b Umehara K. Matsumoto M. Nakamura M. Miyase T. Kuroyanagi M. Noguchi H. Chem. Pharm. Bull. 2000, 48: 566

Suche in Google Scholar
11 Zhang G.-L. Ruecker G. Breitmaier E. Nieger M. Mayer R. Steinbeck C. Phytochemistry 1995, 40: 299

Crossref Suche in Google Scholar
12a Ruggli P. Zickendraht C. Helv. Chim. Acta 1945, 28: 1377

Suche in Google Scholar
12b Bülow R. Koch S. Ber. Dtsch. Chem. Ges. 1904, 37: 579

Suche in Google Scholar
12c Scheiber J. Justus Liebigs Ann. Chem. 1912, 389: 151

Suche in Google Scholar
12d Maruyama K. Osuka A. J. Org. Chem. 1980, 45: 1898

Suche in Google Scholar
For reactions of pseudophthaloyl chloride, see:
12e Naik SN. Pandey B. Ayyangar NR. Synth. Commun. 1988, 18: 625

Suche in Google Scholar
13a Chordia MD. Narasimhan NS. J. Chem. Soc., Perkin Trans. 1 1991, 371
13b Hanack M. Zipplies T. J. Am. Chem. Soc. 1985, 107: 6127

Suche in Google Scholar
13c Kayser MM. Hatt KL. Hooper DL. Can. J. Chem. 1992, 70: 1985

Suche in Google Scholar
13d Abell AD. Hoult DA. Morris KM. Taylor JM. Trent JO. J. Org. Chem. 1993, 58: 1531

Suche in Google Scholar
14 Kundu NG. Pal M. J. Chem. Soc., Chem. Commun. 1993, 86
17 Fischer E. Koch H. Ber. Dtsch. Chem. Ges. 1883, 16: 651

Crossref Suche in Google Scholar
18 Kundu NG. Pal M. Nandi B. J. Chem. Soc., Perkin Trans. 1 1998, 561
19 Renfrew AH. Bostock SB. J. Chem. Soc., Perkin Trans. 1 1977, 84

15

For the AlCl₃-catalyzed transformation of 1 into A, see ref. 12e.

16

CCDC-821844 (5i), CCDC-823020 (5f), CCDC-823021 (6a), and CCDC-824363 (7a) contain all crystallographic details of this publication and are available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.