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Synlett 2012; 23(15): 2274-2278
DOI: 10.1055/s-0032-1317030
DOI: 10.1055/s-0032-1317030
letter
Isocyanide-Based Multicomponent [2+2+1]-Cycloaddition Strategy to Construct Functionalized Spirocyclic Oxindoles
Authors
Further Information
Publication History
Received: 16 June 2012
Accepted: 12 July 2012
Publication Date:
14 August 2012 (online)
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 - oxindolylideneacetateSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information (PDF)
-
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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.