当前位置: X-MOL 学术Org. Lett. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Regioselective Synthesis of 3-Trifluoromethylpyrazole by Coupling of Aldehydes, Sulfonyl Hydrazides, and 2-Bromo-3,3,3-trifluoropropene.
Organic Letters ( IF 4.9 ) Pub Date : 2020-01-17 , DOI: 10.1021/acs.orglett.9b04228
Chuanle Zhu 1 , Hao Zeng 1 , Chi Liu 1 , Yingying Cai 1 , Xiaojie Fang 1 , Huanfeng Jiang 1
Affiliation  

A general and practical strategy for 3-trifluoromethylpyrazole synthesis is reported that occurs by the three-component coupling of environmentally friendly and large-tonnage industrial feedstock 2-bromo-3,3,3-trifluoropropene (BTP), aldehydes, and sulfonyl hydrazides. This highly regioselective three-component reaction is metal-free, catalyst-free, and operationally simple and features mild conditions, a broad substrate scope, high yields, and valuable functional group tolerance. Remarkably, the reactions could be performed on a 100 mmol scale and smoothly afforded the key intermediates for the synthesis of celecoxib, mavacoxib, SC-560, and AS-136A. Preliminary mechanism studies indicated that a 1,3-hydrogen atom transfer process was involved in this transformation.

中文翻译:

通过醛,磺酰肼和2-溴-3,3,3-三氟丙烯的偶联区域选择性合成3-三氟甲基吡唑。

据报道,通过环境友好的大吨位工业原料2-溴-3,3,3-三氟丙烯(BTP),醛和磺酰肼的三组分偶联,可以实现3-三氟甲基吡唑合成的通用和实用策略。这种高度区域选择性的三组分反应不含金属,不含催化剂,操作简单,具有条件温和,底物范围广,收率高和有价值的官能团耐受性。值得注意的是,反应可以在100 mmol的规模上进行,并顺利提供了塞来昔布,马伐昔布,SC-560和AS-136A合成的关键中间体。初步机理研究表明,此转化过程涉及1,3-氢原子转移过程。
更新日期:2020-01-17
down
wechat
bug