M. A. Hossain
Feb 1, 2001
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Journal
ChemInform
Abstract
3-Methoxy-5-hydroxy-3', 4'-methy lened ioxy-6", 6"-d imethy lpyrano[2", 3" : 7. 81 navone 7 has been synthesised from phloroacetophenone 1. Phloroacetophenone 1 on treatment with chlorobutyne (2-chloro-2-methylbut-3-yne) in dry dioxan yields 2, 6-dihydroxy-6', 6'-dimethy lpyrano[2', 3' : 4, 31acetophenone 2 which on treatment with methoxymethy l chloride affords 2, 6-d i (methoxymethoxy)-6'. 6'-dimethy lpyrano[2", 3" : 4', 3'l acelOphenone 3. A lkaline condensation of 3 with piperonal gives 2', 6'-di (methoxymethoxy)-3, 4-methy lened ioxy-6", 6"dimethy lpyrano[2", 3" : 4', 3' Jehalcone 4. Demethoxymethy lat ion of 4 affords 2, 6-d ihydroxy-3 , 4-methy lened ioxy-6", 6"dimethy lpyrano[2", 3" : 4', 3' lchaleone 5 . Chalcone 5 on treatment with H20 1 in pyrid ine furnishes 3, 5-d ihydroxy-3 ', 4'methy lenedioxy-6", 6"-dimethy lpyrano[2", 3" : 7. 81 navone 6 . Fi nally parti al methy lation of 6 gives 3-methoxy-5-hydroxy-3', 4'methy lenedioxy-6", 6"dimethy lpyrano [2", 3" :7, 81navone 7 . A ll the new products have been characterised by the spectral data and elemental analysis.