Microwave-Assisted Improved Regioselective Synthesis of 12H-Benzopyrano[3,2-c][1]benzopyran-5-ones by Radical Cyclisation

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ID: 10994
2011
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Abstract
Two new effective methodologies have been adopted for the preparation of 4-(2′-bromobenzyloxy)benzopyran-7-ones 3(a–h). In the first methodology, 4-hydroxy[1]benzopyran-2-ones 1(a–d) was alkylated with 2-bromobenzyl bromide 2a or 2-bromo-5-methoxy benzyl bromide 2b under phase transfer catalysis condition using lithium hydroxide/tetrabutyl ammonium bromide in N,N-dimethylformamide at 40–50°C and in the second method the microwave irradiation protocol has been exploited by simply mixing of 4-hydroxy[1]benzopyran-2-ones 1(a–d) with 25% excess of 2-bromobenzyl bromide 2a or 2-bromo-5-methoxy benzyl bromide 2b. A catalytic amount of TBAB and potassium carbonate were added and irradiated in an open Erlenmeyer flask in a microwave oven for 4–10 min. The tributyltin-hydride-mediated radical cyclisation of 3(a–h) was carried out under microwave irradiation to generate 12H-benzopyrano[3,2-c][1]benzopyran-5-ones 4(a–h) in 78–88% yield and in this technique yields were significantly improved and reaction time was shortened compared to the previously reported conventional radical cyclisation method.
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kumar2011microwaveassistedorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Basu, Pradipta Kumar;Ghosh, Amrita;Basu, Pradipta Kumar;Ghosh, Amrita;
Journal organic chemistry international
Year 2011
DOI
10.1155/2011/394619
URL
https://www.hindawi.com/journals/oci/2011/394619/abs/
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