NIS促进的氨基环化反应的新见解。由2-烯丙基环己胺合成十氢喹啉。
New insights into NIS-promoted aminocyclization. Synthesis of decahydroquinolines from 2-allylcyclohexylamines.
作者信息
Diaba Faïza, Ricou Eva, Bonjoch Josep
机构信息
Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain.
出版信息
Org Lett. 2007 Jul 5;9(14):2633-6. doi: 10.1021/ol070770g. Epub 2007 Jun 6.
Bishomoallylic secondary amines embodying the 2-allyl-N-benzylcyclohexylamine unit react with NIS to undergo cyclization through 6-endo processes in either the cis or trans series. Nevertheless, when the resulting cis-3-iododecahydroquinolines are treated with Al2O3, the exo derivatives evolve into octahydroindoles and the endo derivatives keep the same backbone, the configuration being retained in the generated alcohols.
含有2-烯丙基-N-苄基环己胺单元的双高烯丙基仲胺与NIS反应，通过顺式或反式系列的6-内型过程进行环化。然而，当所得的顺式-3-碘十氢喹啉用Al2O3处理时，外型衍生物演变成八氢吲哚，而内型衍生物保持相同的主链，构型在生成的醇中得以保留。
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