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SYNTHESIS OF FUNCTIONALIZED 1-METHYLCHROMENO[3,4-b]PYRROL-4(3H)-ONES via THE BARTON–ZARD REACTION STARTING FROM PSEUDONITROSITES

Даниил А. Русанов, Александр В. Самет, Вячеслав В. Русак, Виктор В. Семёнов
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Abstract


A method for the preparation of chromeno[3,4-b]pyrrol-4(3H)-ones via the synthesis of the corresponding 3-arylpyrrole-2-carboxylates from pseudonitrosites by the Barton–Zard reaction was developed. As a result of selective O-demethylation upon exposure to BBr3, the lactone ring closes with the formation of substituted chromeno[3,4-b]pyrrolones in moderate yields.

Keywords


chromeno[3,4-b]pyrrol-4(3H)-ones; lamellarins; propenylbenzenes; pseudonitrosites; Barton–Zard reaction; O-demethylation.

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