A DIELS-ALDER REACTION OF POSSIBLE BIOSYNTHETIC IMPORTANCE
A DIELS-ALDER REACTION OF POSSIBLE BIOSYNTHETIC IMPORTANCE
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DOI：
10.1039/c2970001103a
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发表时间：
1970-01-01
期刊：
影响因子：
--
通讯作者：
SAMMES, PG
中科院分区：
文献类型：
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作者：
PORTER, AEA;SAMMES, PG
BIRCH和WRIGHT最近描述了从短青霉中分离出一类新的化合物。其中之一，短藤酰胺A，被指定为结构（1）。对该式的研究导致这样的假设，即桥连的哌嗪-二酮部分是通过异戊烯基单元和相应的吡嗪酮（例如2）之间的[2+ 41]环加成反应形成的。为了测试这种Diels-Alder反应的可能性，将吡嗪（3; R= H）2在二甲基甲酰胺中在室温下用乙炔二甲酸二甲酯处理。形成双环加合物（4），其在二甲基甲酰胺中在100 ° C下加热15分钟时分解。产品是否被识别？作为异构体吡啶酮（5;
BIRCH and WRIGHT~ recently described the isolation of a new class of compounds from PeniciElium brevi-comfiactum. One of these, brevianamide A, was assigned the structure (1). Examination of this formula leads to the postulate that the bridged piperazine-dione moiety is formed by a [2+ 41 cycloaddition reaction between the isopentenyl unit and the corresponding pyrazinone (eg 2). In order to test the possibility of such a Diels-Alder reaction the pyrazine (3; R= H) 2 was treated with dimethyl acetylenedicarboxylate in dimethylformamide at room temperature. A bicyclic adduct (4) was formed, which decomposed on heating at 100" in dimethylformamide for 15min. The products were identified? as the isomeric pyridones (5;