Some reactions of carbenoids with chromone-2-carboxylic esters

Autor:	John Shipman, Ian Douglas Dicker, John Louis Suschitzky
Rok vydání:	1984
Předmět:	chemistry.chemical_compound Chloroacetone chemistry Bicyclic molecule Cyclopropanation Stereochemistry Yield (chemistry) Furan Chromone Ring (chemistry) Carbenoid
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :487
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19840000487
Popis:	Ethyl 5-hydroxy-4-oxo-8-propyl-4H-[1]benzopyran-2-carboxylate (3a) reacts with chloroacetone under basic conditions to yield (1α, 1aα, 7aα)- and (1β, 1aα, 7aα)-ethyl 1-acetyl-1,1a,7,7a-tetrahydro-6-hydroxy-7-oxo-3-propylbenzo[b]cyclopropa[e]pyran-1a-carboxylate (4a) and (5a), products of cyclo-propanation of the chromone 2,3-double bond, as well as ethyl 1,7-diacetyl-7, 7a-dihydro-5-propyl-6aH-cyclopropa[b]furo[4,3,2-de][1]benzopyran-6a-carboxylate (6a), representing a novel ring system. The corresponding tetrahydronaphthopyran (3b) gives analogous products (4b), (5b), and (6b). The thiochromone analogue of (3a), (8), gives only the furan annelated product ethyl 2-acetyl-6-propylthio-pyrano[4,3,2-cd]benzofuran-4-carboxylate (9) under similar conditions. The reaction of the chromone (3b) with dimethylsulphoxonium methylide to yield the isomeric naphthofuranones (16a) and (17a) is also described.
Databáze:	OpenAIRE
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