Synthesis and cross-coupling reactions of 7-azaindoles via a new donor - Acceptor cyclopropane
Synthesis and cross-coupling reactions of 7-azaindoles via a new donor - Acceptor cyclopropane
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DOI：
10.1021/ol061379i
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发表时间：
2006-08-17
期刊：
影响因子：
5.2
通讯作者：
Kerr, Michael A.
中科院分区：
文献类型：
--
作者：
Zheng, Xiaomei;Kerr, Michael A.
从市售的环丙烷-1，1-二酯制备了一种新型的给体-受体环丙烷。该环丙烷与三氟甲磺酸酐反应产生可分离的三氟甲氧基中间体，当用伯胺处理时，该中间体得到6-三氟甲氧基-7-氮杂吲哚啉，该6-三氟甲氧基-7-氮杂吲哚啉又可以脱氢成氮杂吲哚。6-trifloxy取代基可用于通过各种交叉偶联反应在该位置引入多样性，从而制备基于重要的7-氮杂吲哚药效团的潜在感兴趣的化合物。
A new type of donor-acceptor cyclopropane has been prepared from commercially available cyclopropane- 1,1-diesters. This cyclopropane reacts with triflic anhydride to produce an isolable tristrifloxy intermediate which when treated with primary amines gives 6-trifloxy-7-azaindolines which in turn can be dehydrogenated to the azaindoles. The 6-trifloxy substituent can be used to introduce diversity at this position via a variety of cross-coupling reactions thus preparing potentially interesting compounds based on the important 7-azaindole pharmacophore.