^‡ Both authors contributed equally to this work.

Abstract

Diastereoselective Diels–Alder reactions of 2,6-diaryl-1,2-dihydropyridines with N-methylmaleimide afford highly substituted isoquinuclidines in good chemical yield (30–50%). This sequential one-pot synthesis is performed under microwave irradiation and involves, primarily, the synthesis of 2,6-diaryl-1,2-dihydropyridines by a 6π-azaelectrocyclisation involving an intermediate α,β,γ,δ-di-unsaturated imine, obtained by condensation of (E,E)-cinnamylideneacetophenones with amines. This procedure easily converts unstable 2,6-diaryl-1,2-dihydropyridines into, otherwise inaccessible, isoquinuclidines without any kind of manipulation.

Diastereoselective Diels–Alder reactions of 2,6-diaryl-1,2-dihydropyridines with N-methylmaleimide afford highly substituted isoquinuclidines in good chemical yield (30–50%). This sequential one-pot synthesis is performed under microwave irradiation and involves, primarily, the synthesis of 2,6-diaryl-1,2-dihydropyridines by a 6π-azaelectrocyclisation involving an intermediate α,β,γ,δ-di-unsaturated imine, obtained by condensation of (E,E)-cinnamylideneacetophenones with amines. This procedure easily converts unstable 2,6-diaryl-1,2-dihydropyridines into, otherwise inaccessible, isoquinuclidines without any kind of manipulation.

中文翻译：

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以（E，E）-肉桂亚基苯乙酮为模板通过2,6-二芳基-1,2-二氢吡啶一锅合成异喹啉

^‡两位作者均对这项工作做出了同等贡献。

抽象的

2,6-二芳基-1,2-二氢吡啶与N-甲基马来酰亚胺的非对映选择性Diels-Alder反应可得到高度取代的异喹核苷，化学收率很好（30-50％）。该顺序一锅合成是在微波辐射下进行的，主要涉及通过6π-氮杂电环化反应合成2,6-二芳基-1,2-二氢吡啶，涉及中间体α，β，γ，δ-二不饱和亚胺。 ，是通过（E，E）-肉桂亚甲基苯乙酮与胺的缩合反应而获得的。该方法可以容易地将不稳定的2,6-二芳基-1,2-二氢吡啶类转化为异喹啉类，否则很难获得，而无需进行任何操作。

2,6-二芳基-1,2-二氢吡啶与N-甲基马来酰亚胺的非对映选择性Diels-Alder反应可得到高度取代的异喹核苷，化学收率很好（30-50％）。该顺序一锅合成是在微波辐射下进行的，主要涉及通过6π-氮杂电环化反应合成2,6-二芳基-1,2-二氢吡啶，涉及中间体α，β，γ，δ-二不饱和亚胺。 ，是通过（E，E）-肉桂亚甲基苯乙酮与胺的缩合反应而获得的。该方法可以容易地将不稳定的2,6-二芳基-1,2-二氢吡啶类转化为异喹啉类，否则很难获得，而无需进行任何操作。