A Base-Catalyzed, Domino Aldol/hetero-Diels–Alder Synthesis of Tricyclic Pyrano[3,4-c]chromenes in Glycerol
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- 作者：Bhagyashri D. Parmar ; Tushar R. Sutariya ; Gaurangkumar C. Brahmbhatt ; Narsidas J. Parmar ; Rajni Kant ; Vivek K. Gupta
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：June 17, 2016
- 年：2016
- 卷：81
- 期：12
- 页码：4955-4964
- 全文大小：509K
- 年卷期：0
- ISSN：1520-6904
文摘
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.