A Base-Catalyzed, Domino Aldol/hetero-Diels–Alder Synthesis of Tricyclic Pyrano[3,4‑c]chromenes in Glycerol

The domino aldol/hetero-Diels–Alder synthesis of some new tricyclic pyrano­[3,4-c]­chromene derivatives has been achieved successfully after assembling a variety of acyclic or cyclic monoketones with prenyl ether-tethered aldehydes in the presence of 1,8-diazabicyclo[5.4.0]­undec-7-ene in glycerol a...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-06, Vol.81 (12), p.4955-4964
Main Authors: Parmar, Bhagyashri D, Sutariya, Tushar R, Brahmbhatt, Gaurangkumar C, Parmar, Narsidas J, Kant, Rajni, Gupta, Vivek K
Format: Article
Language:English
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Summary:The domino aldol/hetero-Diels–Alder synthesis of some new tricyclic pyrano­[3,4-c]­chromene derivatives has been achieved successfully after assembling a variety of acyclic or cyclic monoketones with prenyl ether-tethered aldehydes in the presence of 1,8-diazabicyclo[5.4.0]­undec-7-ene in glycerol at 120 °C. The hitherto unreported stereochemical outcome of this synthetic sequence was studied and established on the basis of single-crystal X-ray diffraction data and 2D NMR NOESY spectroscopy along with the isolation and characterization of the intermediate Aldol condensation product.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00107