1007652-06-3Relevant academic research and scientific papers
Preparation method of ortho-amino trifluoroacetophenone and derivatives thereof
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Paragraph 0041; 0045-0048, (2021/11/19)
The invention relates to the field of organic synthesis, in particular to a preparation method of ortho-amino trifluoroacetophenone and derivatives thereof. The preparation of ortho-amino trifluoroacetophenone comprises three steps of amino protection, trifluoroacetylation and deprotection, the overall reaction condition is mild, the yield is high, and the method is suitable for large-scale production. In addition, on the basis of the preparation, substitution is carried out after amino diazotization, the ortho-amino trifluoroacetophenone derivative is further prepared, and the industrial application prospect is good.
Site-Selective C–H Functionalization of (Hetero)Arenes via Transient, Non-symmetric Iodanes
Fosu, Stacy C.,Hambira, Chido M.,Chen, Andrew D.,Fuchs, James R.,Nagib, David A.
supporting information, p. 417 - 428 (2019/02/14)
Fosu, Hambira, and colleagues describe the direct C–H functionalization of medicinally relevant arenes or heteroarenes. This strategy is enabled by transient generation of reactive, non-symmetric iodanes from anions and PhI(OAc)2. The site-selective incorporation of Cl, Br, OMs, OTs, and OTf to complex molecules, including within medicines and natural products, can be conducted by the operationally simple procedure included herein. A computational model for predicting site selectivity is also included. The discovery of new medicines is a time- and labor-intensive process that frequently requires over a decade to complete. A major bottleneck is the synthesis of drug candidates, wherein each complex molecule must be prepared individually via a multi-step synthesis, frequently requiring a week of effort per molecule for thousands of candidates. As an alternate strategy, direct, post-synthetic functionalization of a lead candidate could enable this diversification in a single operation. In this article, we describe a new method for direct manipulation of drug-like molecules by incorporation of motifs with either known pharmaceutical value (halides) or that permit subsequent conversion (pseudo-halides) to medicinally relevant analogs. This user-friendly strategy is enabled by combining commercial iodine reagents with salts and acids. We expect this simple method for selective, post-synthetic incorporation of molecular diversity will streamline the discovery of new medicines. A strategy for C–H functionalization of arenes and heteroarenes has been developed to allow site-selective incorporation of various anions, including Cl, Br, OMs, OTs, and OTf. This approach is enabled by in situ generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc)2. The utility of this mechanism is demonstrated via para-selective chlorination of medicinally relevant arenes, as well as site-selective C–H chlorination of heteroarenes. Spectroscopic, computational, and competition experiments describe the unique nature, reactivity, and selectivity of these transient, unsymmetrical iodanes.
CuCl-catalyzed ortho trifluoromethylation of arenes and heteroarenes with a pivalamido directing group
Cai, Shangjun,Chen, Chao,Sun, Zelin,Xi, Chanjuan
supporting information, p. 4552 - 4554 (2013/06/04)
The CuCl catalyzed direct trifluoromethylation of sp2 C-H bonds has been realized, using the Togni reagent as the CF3 source. This reaction achieves the goal of regio-selectively converting C-H into C-CF 3 with ecological and readily available starting materials.
Discovery of atrop fixed alkoxy-aminobenzhydrol derivatives: Novel, highly potent and orally efficacious squalene synthase inhibitors
Ichikawa, Masanori,Yokomizo, Aki,Itoh, Masao,Haginoya, Noriyasu,Sugita, Kazuyuki,Usui, Hiroyuki,Terayama, Koji,Kanda, Akira
experimental part, p. 5207 - 5224 (2011/10/08)
We have recently reported the discovery of the new benzhydrol template, which has a highly potent inhibitory activity for squalene synthase, as typified by compound 1 (SSI IC50 = 0.85 nM). However, it was composed of a pair of easy rotatable at
