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A new domino Knoevenagel-hetero-Diels-Alder reaction: An efficient catalyst-free synthesis of novel thiochromone-annulated thiopyranocoumarin derivatives in aqueous medium

Matloubi Moghaddam, F ; Sharif University of Technology | 2010

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Type of Document: Article
DOI: 10.1016/j.tet.2010.09.048
Publisher: 2010
Abstract:
An efficient catalyst-free synthesis of novel pentacyclic thiochromone-annulated thiopyranocoumarin derivatives is achieved via domino Knoevenagel-hetero-Diels-Alder reaction of 4-hydroxy dithiocoumarin and O-acrylated salicylaldehyde derivatives in H2O as solvent. The products are formed in good yields with high regio- and stereo-selectivity
Keywords:
3,4-Dihydrocoumarine ; Aqueous medium ; Domino reaction ; Knoevenagel-hetero-Diels-Alder ; O-acrylated salicylaldehyde ; Thiopyran ; 2 bromo 7 phenyl 6a,14b dihydro 6h,7h,14h thiochromeno[3',2':5,6]thiopyrano[3,4 c]chromene 6,14 dione ; 2 nitro 7 phenyl 6a,14b dihydro 6h,7h,14h thiochromeno[3',2':5,6]thiopyrano[3,4 c]chromene 6,14 dione ; 4 methoxy 7 phenyl 6a,14b dihydro 6h,7h,14h thiochromeno[3',2':5,6]thiopyrano[3,4 c]chromene 6,14 dione ; 7 methyl 2 nitro 6a,14b dihydro 6h,7h,14h thiochromeno[3',2':5,6]thiopyrano[3,4 c]chromene 6,14 dione ; 7 phenyl 6a,14b dihydro 6h,7h,14h thiochromeno[3',2':5,6]thiopyrano[3,4 c]chromene 6,14 dione ; Chromone derivative ; Pyranocoumarin derivative ; Salicylaldehyde ; Solvent ; Unclassified drug ; Water ; Aqueous solution ; Catalyst ; Diels Alder reaction ; Drug synthesis ; Knoevenagel condensation ; Priority journal ; Stereochemistry ; Alnus
Source: Tetrahedron ; Volume 66, Issue 45 , November , 2010 , Pages 8615-8622 ; 00404020 (ISSN)
URL: http://www.sciencedirect.com/science/article/pii/S0040402010013852