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Synlett 2012; 23(15): 2274-2278
DOI: 10.1055/s-0032-1317030
letter
© Georg Thieme Verlag Stuttgart · New York

Isocyanide-Based Multicomponent [2+2+1]-Cycloaddition Strategy to Construct Functionalized Spirocyclic Oxindoles

Haohua Jie
a   Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China, Fax: +86(21)66132408   Email: lijian@shu.edu.cn
,
Jian Li*
a   Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China, Fax: +86(21)66132408   Email: lijian@shu.edu.cn
,
Chunju Li
a   Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China, Fax: +86(21)66132408   Email: lijian@shu.edu.cn
,
Xueshun Jia*
a   Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China, Fax: +86(21)66132408   Email: lijian@shu.edu.cn
b   Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, Email: xsjia@mail.shu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 16 June 2012

Accepted: 12 July 2012

Publication Date:
14 August 2012 (online)

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Abstract

Isocyanide-based three-component [2+2+1]-cyclo­addition reactions from isocyanides, activated alkynes, and isatylidene malononitriles were investigated to provide a new access to spirocyclic oxindole with five-membered carbon rings. The displacement of isatylidene malononitrile with oxindolylideneacetate essentially results in opposite regioselectivity, which adds to its ­attractiveness.

Key words

isocyanide - activated alkyne - isatylidene malono­nitrile - spirocyclic oxindole - oxindolylideneacetate

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

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  • 14 See the Supporting Information for details
  • 15 CCDC 884218 (4b) and CCDC 884219 (4f) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif
  • 16 CCDC 884217 for compound 7a contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif
  • 17 General Experimental Procedure for 4: Isatylidene malononitrile 3 (0.5 mmol) was added to a solution of isocyanide 1 (0.5 mmol) and alkynoate 2 (0.6 mmol) in toluene (5 mL). The stirred mixture was heated to 100 °C for several hours and the progress of the reaction was monitored by TLC. Upon completion, the reaction mixture was concentrated under vacuum. The residue was purified by column chromatography on silica gel (silica: 200–300; PE–EtOAc) to afford the desired product 4. Compound 4a: Yellow solid; mp 194–196 °C. 1H NMR (500 MHz, CDCl3): δ = 7.53 (t, J = 7.5 Hz, 1 H), 7.46 (d, J = 7.5 Hz, 1 H), 7.22 (t, J = 7.5 Hz, 1 H), 7.11–7.03 (m, 4 H), 6.86 (s, 1 H), 4.05–3.94 (m, 2 H), 3.37 (s, 3 H), 2.20 (s, 6 H), 1.00 (t, J = 7.0 Hz, 3 H). 13C NMR (125 MHz, CDCl3): δ = 170.6, 161.8, 161.0, 149.7, 146.4, 144.8, 131.7, 131.5, 128.4, 126.6, 125.7, 125.4, 123.9, 123.1, 111.7, 110.6, 109.5, 68.3, 62.5, 62.4, 48.8, 38.9, 18.0, 13.7. HRMS: m/z [M + Na]+ calcd for C26H22N4O3: 461.1590; found: 461.1595.