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

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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Veröffentlicht in:Journal of organic chemistry 2016-06, Vol.81 (12), p.4955-4964
Hauptverfasser: Parmar, Bhagyashri D, Sutariya, Tushar R, Brahmbhatt, Gaurangkumar C, Parmar, Narsidas J, Kant, Rajni, Gupta, Vivek K
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container_end_page 4964
container_issue 12
container_start_page 4955
container_title Journal of organic chemistry
container_volume 81
creator Parmar, Bhagyashri D
Sutariya, Tushar R
Brahmbhatt, Gaurangkumar C
Parmar, Narsidas J
Kant, Rajni
Gupta, Vivek K
description 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.
doi_str_mv 10.1021/acs.joc.6b00107
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title A Base-Catalyzed, Domino Aldol/hetero-Diels–Alder Synthesis of Tricyclic Pyrano[3,4‑c]chromenes in Glycerol
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