Tomakinian Terry, Guillot Régis, Kouklovsky Cyrille, Vincent Guillaume
Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques (MS&MT), Univ Paris Sud, CNRS, Université Paris-Saclay, 91405, Orsay, France.
Chem Commun (Camb). 2016 Apr 7;52(31):5443-6. doi: 10.1039/c6cc00365f.
We report the access to the benzofuro[3,2-b]indoline framework of phalarine from benzofuran-2-ones via the Fischer indolization reaction which was interrupted at the deamination step. Unexpectedly, allyl nucleophiles did not add to the aminal position of these benzofuro[3,2-b]indoline amines but to the adjacent ring junction center in the presence of trifluoroborane to deliver 3,3-disubstituted indolines containing a difluoroboron-containing six-membered ring with fluorescence properties.
我们报道了通过费歇尔吲哚合成反应从苯并呋喃 -2- 酮获得法拉林的苯并呋喃并[3,2 -b]吲哚啉骨架，该反应在脱氨基步骤中被中断。出乎意料的是，在三氟化硼存在下，烯丙基亲核试剂不会加到这些苯并呋喃并[3,2 -b]吲哚啉胺的氨基位置，而是加到相邻的环连接中心，从而得到含有含二氟化硼六元环且具有荧光性质的 3,3 - 二取代吲哚啉。
