Substitution Alters the Mode
of Molecular Iodine-Mediated Intramolecular Cyclization: Syntheses
of Benzoxepine and Benzo-2H-pyran Derivatives

Krishna C. Majumdar; Inul Ansary; Biswajit Sinha; Brindaban Roy; Balasubramanian Sridhar

doi:10.1055/s-0030-1260196

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

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2011(20): 3287-3296
DOI: 10.1055/s-0030-1260196

PAPER

Substitution Alters the Mode of Molecular Iodine-Mediated Intramolecular Cyclization: Syntheses of Benzoxepine and Benzo-2H-pyran Derivatives

Krishna C. Majumdar*^a, Inul Ansary^a, Biswajit Sinha^a, Brindaban Roy^a, Balasubramanian Sridhar^b
^a Department of Chemistry, University of Kalyani, Kalyani 741235, West Bengal, India
Fax: +91(33)25828282; e-Mail: kcm_ku@yahoo.co.in;
^b Laboratory of X-ray Crystallography, IICT, Hyderabad 500007, India

Further Information

Publication History

Received 25 June 2011
Publication Date:
01 September 2011 (online)

Abstract
Full Text
References

Buy Article Permissions and Reprints All articles of this category

Abstract

The synthesis of benzoxepine and benzo-2H-pyran derivatives by the implementation of an inxepensive and easy to handle molecular iodine-mediated intramolecular electrophilic cyclization strategy is described. Simple substitution at the terminus of the propargyl group alters the course of the iodocyclization.

Key words

iodine - intramolecular cyclization - benzoxepine - benzo-2H-pyrans

References

2 Li C. Lee D. Graf TN. Phifer SS. Nakanishi Y. Riswan S. Setyowati FM. Saribi AM. Soejarto DD. Farnsworth NR. Falkinham JO. Kroll DJ. Kinghorn AD. Wani MC. Oberlies NH. J. Nat. Prod. 2009, 72: 1949

Crossref Search in Google Scholar
3 Fan X. Zi J. Zhu C. Xu W. Cheng W. Yang S. Guo Y. Shi J. J. Nat. Prod. 2009, 72: 1184

Crossref Search in Google Scholar
4 Flick AC. Caballero MJA. Padwa A. Org. Lett. 2008, 10: 1871

Crossref Search in Google Scholar
5a Zhendong J, and Ying K. inventors; PCT Int. Appl. WO 2004058738.
5b Iwata N. Wang N. Yao X. Kitanaka S. J. Nat. Prod. 2004, 67: 1106

Search in Google Scholar
5c Hu H. Harrison TJ. Wilson PD. J. Org. Chem. 2004, 69: 3782

Search in Google Scholar
6 Korec R. Sensch KH. Zoukas T. Arzneim. Forsch. 2000, 50: 122

Search in Google Scholar
7 Bonadies F. Di Fabio R. Bonini C. J. Org. Chem. 1984, 49: 1647

Crossref Search in Google Scholar
8 Morandim AA. Bergamo DCB. Kato MJ. Cavalheiro AJ. Bolzani VS. Furlan M. Phytochem. Anal. 2005, 16: 282

Crossref PubMed Search in Google Scholar
9 Stefan B. Larsson LG. Rényi L. Ross SB. Thorberg S.-O. Thorell-Svantesson G. J. Med. Chem. 1998, 41: 1934

Crossref Search in Google Scholar
10 Ishizuka N. Matsumura K. Sakai K. Fujimoto M. Mihara S. Yamamori T. J. Med. Chem. 2002, 45: 2041

Crossref Search in Google Scholar
11a TenBrink RE. McCall JM. Johnson HG. J. Med. Chem. 1980, 23: 1058

Search in Google Scholar
11b TenBrink RE. McCall JM. Pals DT. McCall RB. Orley J. Humphrey SJ. Wendling MG. J. Med. Chem. 1981, 24: 64

Search in Google Scholar
11c O’Shea DF. Sharp JT. J. Chem. Soc., Perkin Trans. 1 1995, 515
11d Tretter JR. inventors; US Patent 3514449. ; Chem. Abstr. 1970, 73, 35404u
11e Dictionary of Drugs 1st ed.: Elks J. Ganellin CR. Chapman and Hall; London: 1990. p.984
12a Engler M. Anke T. Sterner O. Brandt U. J. Antibiot. 1997, 50: 325

Search in Google Scholar
12b Wijnberg JBPA. van Veldhuizen A. Swart HJ. Frankland JC. Field JA. Tetrahedron Lett. 1999, 40: 5767

Search in Google Scholar
13 Lin YL. Kuo HS. Wang YW. Huang ST. Tetrahedron 2003, 59: 1277

Crossref Search in Google Scholar
14a Di Fabio R. Micheli F. Baraldi D. Bertani B. Conti N. Dal Forno G. Feriani A. Donati D. Marcchioro C. Messeri T. Missio A. Pasquarello A. Pentassuglia G. Pizzi DA. Provera S. Quaglia AM. Sabbatini FM. Farmaco 2003, 58: 723

Search in Google Scholar
14b Gibson SE. Jones JO. Kalindjinan SB. Knight JD. Steed JW. Tozer MJ. J. Chem. Soc., Chem. Commun. 2002, 1938
14c Alcaide B. Polanco C. Sierra MA. Eur. J. Org. Chem. 1998, 2913
14d Gibson SE. Middleton RJ. J. Chem. Soc., Chem. Commun. 1995, 1743
14e Majumdar KC. Chattopadhyay B. Sinha B. Tetrahedron Lett. 2008, 49: 1319

Search in Google Scholar
14f Majumdar KC. Chattopadhyay B. Synlett 2008, 979
14g Majumdar KC. Chattopadhyay B. Curr. Org. Chem. 2009, 13: 731

Search in Google Scholar
14h Zeni G. Larock RC. Chem. Rev. 2004, 104: 2285

Search in Google Scholar
14i Deiters A. Martin SF. Chem. Rev. 2004, 104: 2199

Search in Google Scholar
14j Chattopadhyay SK. Karmakar S. Biswas T. Majumdar KC. Rahaman H. Roy B. Tetrahedron 2007, 63: 3919

Search in Google Scholar
14k Rosillo M. Domínguez G. Casarrubios L. Pérez-Castells J. J. Org. Chem. 2005, 70: 10611

Search in Google Scholar
14l Trost BM. Homogeneous Transition Metal Catalyzed Reactions Moser WR. Slocum DW. ACS; Washington/DC: 1992. Chap. 31. p.463
15 Patil NT. Yamamoto Y. Chem. Rev. 2008, 108: 3395

Crossref PubMed Search in Google Scholar
For oxygen heterocycles, see:
16a El-Taeb GMM. Evans AB. Knight DW. Jones S. Tetrahedron Lett. 2001, 42: 5945

Search in Google Scholar
16b Arcadi A. Cacchi S. Fabrizi G. Marinelli F. Moro L. Synlett 1999, 1432
For nitrogen heterocycles, see:
16c Knight DW. Redfern AL. Gilmore J. J. Chem. Soc., Perkin Trans. 1 2001, 2874
16d Knight DW. Redfern AL. Gilmore J. J. Chem. Soc., Perkin Trans. 1 2002, 622
16e Flynn BL. Flynn GP. Hamel E. Jung MK. Bioorg. Med. Chem. Lett. 2001, 11: 2341

Search in Google Scholar
16f Ren X.-F. Turos E. Lake CH. Churchill MR. J. Org. Chem. 1995, 60: 6468

Search in Google Scholar
16g Ren X.-F. Konaklieva MI. Shi H. Dickey S. Lim DV. Gonzalez J. Turos E. J. Org. Chem. 1998, 63: 8898

Search in Google Scholar
17a Fischer D. Tomeba H. Pahadi NK. Patil NT. Yamamoto Y. Angew. Chem. Int. Ed. 2007, 46: 4764

Search in Google Scholar
17b Yue D. Yao T. Larock RC. J. Org. Chem. 2006, 71: 62

Search in Google Scholar
17c Yue D. Larock RC. J. Org. Chem. 2002, 67: 1905

Search in Google Scholar
17d He Z. Li H. Li Z. J. Org. Chem. 2010, 75: 4636

Search in Google Scholar
17e Banwell MG. Wills AC. Hamel E. Aust. J. Chem. 1999, 52: 767

Search in Google Scholar
17f Flynn BL. Verdier-Pinard P. Hamel E. Org. Lett. 2001, 3: 651

Search in Google Scholar
17g Larock RC. Yue D. Tetrahedron Lett. 2001, 42: 6011

Search in Google Scholar
17h Hessian KO. Flynn BL. Org. Lett. 2003, 5: 4377

Search in Google Scholar
17i Kesharwani T. Worlikar SA. Larock RC. J. Org. Chem. 2006, 71: 2307

Search in Google Scholar
17j Bui CT. Flynn BF. J. Comb. Chem. 2006, 8: 163

Search in Google Scholar
18a Djuardi E. McNelis E. Tetrahedron Lett. 1999, 40: 7193

Search in Google Scholar
18b Sniady A. Wheeler KA. Dembinski R. Org. Lett. 2005, 7: 1769

Search in Google Scholar
18c Yao T. Zhang X. Larock RC. J. Org. Chem. 2005, 70: 7679

Search in Google Scholar
18d Xie Y.-X. Liu X.-Y. Wu L.-Y. Han Y. Zhao L.-B. Fan M.-J. Liang Y.-M. Eur. J. Org. Chem. 2008, 1013
18e Barluenga J. Trincado M. Rublio E. Gonzalez JM. Angew. Chem. Int. Ed. 2003, 42: 2406

Search in Google Scholar
18f Amjad M. Knight DW. Tetrahedron Lett. 2004, 45: 539

Search in Google Scholar
18g Yue D. Larock RC. Org. Lett. 2004, 6: 1037

Search in Google Scholar
18h Barluenga J. Vazque-Villa H. Ballesteros A. Gonzalez JM. J. Am. Chem. Soc. 2003, 125: 9028

Search in Google Scholar
18i Yue D. Della CaN. Larock RC. Org. Lett. 2004, 6: 1581

Search in Google Scholar
19a Shin S. Gupta AK. Rhim CY. Oh CH. Chem. Commun. 2005, 4429
19b Hildebrandt D. Hüggenberg H. Kanthak M. Plöger T. Müller IM. Dyker G. Chem. Commun. 2006, 2260
19c Kim N. Kim Y. Park W. Sung D. Gupta AK. Oh CH. Org. Lett. 2005, 7: 5289

Search in Google Scholar
19d Padwa A. Fryxell GE. Zhi L. J. Am. Chem. Soc. 1990, 118: 3100

Search in Google Scholar
19e Feldman KS. Tetrahedron Lett. 1983, 24: 5585

Search in Google Scholar
20 Majumdar KC. Sinha B. Ansary I. Chakravorty S. Synlett 2010, 1407

Thieme Connect
21 Worlikar SA. Kesharwani T. Yao T. Larock RC.
J. Org. Chem. 2007, 72: 1347

Crossref PubMed Search in Google Scholar
22 Majumdar KC. Ansary I. Sinha B. Chattopadhyay B. Synthesis 2009, 3593

Thieme Connect
24 Liu W. Zhou S. Org. Lett. 2005, 7: 4609

Crossref PubMed Search in Google Scholar

1

Present address: Department of Chemical Science, Tezpur University, Napaam 784028, Assam, India.

23

CCDC 809665 contains the supplementary crystallographic data for 10a.