Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India.
J Org Chem. 2012 Sep 21;77(18):8191-205. doi: 10.1021/jo301572p. Epub 2012 Sep 4.
An efficient approach for the copper-catalyzed regioselective tandem synthesis of diversely substituted indolo[2,1-a]isoquinolines 11a-r, pyrrolo[2,1-a]isoquinolines 12a-d, and indolo-, pyrrolo[2,1-f][1,6]naphthyridines 14a-f via preferential addition of the heterocyclic amines onto the ortho-haloarylalkynes over N-arylation followed by intramolecular C-2 arylation is described. The scope of the developed chemistry was successfully extended for the direct synthesis of bisindolo-, pyrrolo[2,1-a]isoquinolines 15a-g, a regioisomer of the bisindolo[1,2-a]quinolines used as organic single-crystal field-effect transistor. Hydroxymethyl benzotriazole, which is an inexpensive and air stable compound, has been used as a ligand to carry out this one-step conversion of simple, readily available starting materials into an interesting class of heterocyclic compounds.
一种高效的方法，用于铜催化的区域选择性串联合成各种取代的吲哚并[2,1-a]异喹啉 11a-r、吡咯并[2,1-a]异喹啉 12a-d 和吲哚、吡咯并[2,1-f][1,6]萘啶 14a-f，通过优先将杂环胺加成到邻卤芳基炔烃上，而不是通过 N-芳基化进行 N-芳基化，然后进行分子内 C-2 芳基化。所开发的化学的范围成功扩展到直接合成双吲哚并、吡咯并[2,1-a]异喹啉 15a-g，这是用作有机单晶场效应晶体管的双吲哚并[1,2-a]喹啉的区域异构体。羟甲基苯并三唑是一种廉价且稳定的空气化合物，已被用作配体，将简单、易得的起始原料一步转化为一类有趣的杂环化合物。
