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Catalyst-free [3 + 2] cyclization of imines and Morita–Baylis–Hillman carbonates: a general route to tetrahydropyrrolo[2,1-a]isoquinolines and dihydropyrrolo[2,1-a]isoquinolines
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2017-07-24 00:00:00 , DOI: 10.1039/c7qo00492c
Xue Tang 1, 2, 3, 4, 5 , Ming-Cheng Yang 1, 2, 3, 4, 5 , Cui Ye 1, 2, 3, 4, 5 , Li Liu 1, 2, 3, 4, 5 , Hai-Lin Zhou 6, 7, 8, 9 , Xiao-Jie Jiang 6, 7, 8, 9 , Xiao-Lin You 6, 7, 8, 9 , Bo Han 1, 2, 3, 4, 5 , Hai-Lei Cui 6, 7, 8, 9
Affiliation  

We have developed a mild and efficient catalyst-free [3 + 2] cyclization of isoquinoline imines and Morita–Baylis–Hillman carbonates. Various tetrahydropyrrolo[2,1-a]isoquinolines can be prepared in acceptable to excellent yields (up to 96%). The treatment of tetrahydropyrroloisoquinolines with DDQ afforded 5,6-dihydropyrrolo[2,1-a]isoquinolines in good yields (up to 90%). A one-pot synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines has been achieved successfully (up to 86% yield). It should be noted that all the [3 + 2] cyclization, oxidation and one-pot reactions can be easily scaled up to the gram scale.

中文翻译:

亚胺和Morita–Baylis–Hillman碳酸盐的无催化剂[3 + 2]环化:四氢吡咯并[2,1- a ]异喹啉和二氢吡咯并[2,1- a ]异喹啉的一般路线

我们已经开发出温和而有效的,无催化剂的异喹啉亚胺和Morita–Baylis–Hillman碳酸盐的[3 + 2]环化反应。可以以可接受的产率制备各种四氢吡咯并[2,1- a ]异喹啉(最高96%)。用DDQ处理四氢吡咯并异喹啉可以高产率(高达90%)得到5,6-二氢吡咯并[2,1- a ]异喹啉。一锅合成5,6-二氢吡咯并[2,1- a ]异喹啉已成功实现(最高收率86%)。应该注意的是,所有的[3 + 2]环化,氧化和一锅法反应都可以轻松放大至克级。
更新日期:2017-10-25
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