- Using weak interactions to control C-H mono-nitration of indolines
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An unprecedented C-H mononitration of indolines either at the -C5 or -C7 positions under mild condition is reported here. The roles of multiple weak interactions and factors such as steric factors, electronic effects, cation-π interactions, and solvent polarity were established, and we achieved a 100% regioselective electrophilic aromatic (EArS) nitration using Cu(NO3)2 or AgNO3.
- Bose, Anima,Mal, Prasenjit
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- Regioselective C5 nitration of N-protected indolines using ferric nitrate under mild conditions
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An efficient and facile process has been developed for the regioselective C5 nitration of the N-protected indolines using ferric nitrate as the nitrating reagents. The reaction proceeded smoothly in moderate to excellent yields with high efficiency and broad substrate scope under mild conditions. In addition, the synthesized nitration products can be further transformed to 5-nitroindolines and C5-nitroindole derivatives. The method is operationally simple, efficient, and might have potential application in industry production.
- Li, Dandan,Chen, Yimeng,Ma, Mengya,Yu, Yanling,Jia, Zhenzhen,Li, Penghui,Xie, Zhiyu
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- Indole derivatives or salts thereof as well as preparation method and application of indole derivatives or salts thereof
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The invention belongs to the technical field of chemical medicine, and relates to an Hh (Hedgehog) signal pathway Smoothed (SMO) receptor small molecule inhibitor, in particular to indole derivativesor salts thereof with Smoothed inhibitory activity, which are shown in chemical general formula (I) in the description, as well as a preparation method and pharmaceutical composition of the indole derivatives or salts thereof. Tests on inhibitory activity of Hh signal pathways show that most compounds have better inhibitory activity on the Hh signal pathways. The invention further discloses the application of the compounds to preparation of medicines for treating diseases associated with Hh, wherein the diseases are BCC (basal cell carcinoma), MB (medullblastoma), SCLC (small cell lung cancer), medulloblastoma, rhabdomyosarcoma, or a combination of the diseases.
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Paragraph 0149; 0152-0153; 0188; 0191; 0192
(2019/02/06)
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- C5 nitration method of indoline compound
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The invention discloses a C5 nitration method of an indoline compound. According to the method, cheap copper salt is used as a catalyst, organic small molecular tert-butyl nitrite (TBN) is used as a metal-free nitro source, and the air is used as an oxidizing agent. The above materials are subjected to C5 C-H functionalization in an organic solvent so as to realize C5 C-H nitration of the indolinecompound and obtain the C5 nitrated indoline compound. The method of the invention has advantages of simple reaction operation, low reaction cost, high yield, mild condition, no heavy metal pollution, etc.
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Paragraph 0050-0052
(2019/08/30)
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- Synthesis method for acylindoline-type compound with C-5 position substituted by nitro group
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The invention discloses a synthesis method for an acylindoline-type compound with a C-5 position substituted by a nitro group, wherein a reaction general formula is represented as follows, R referring to alkyl groups including hydrogen (H), 4-methyl and 7-methyl groups. The synthesis method is simple and high-effective, wherein by means of ferric nitrate nonahydrate, the acylindoline-type compound with the C-5 position substituted by a nitro group is produced directly through one step. The reaction has strong zone selectivity and high synthesis efficiency. The raw materials are easy to prepare, and the nitration reagent, ferric nitrate nonahydrate, is low-cost and easy-to-obtained, has wide source and is stable and low-toxic. The reaction is free of protection by inert gas and can be directly carried out in air, has simple operations and gentle conditions, employs a low-cost and easy-to-obtained solvent, and has wide adaptable range of a substrate. The method is low in requirement on reaction conditions, has wide adaptable range, has significant advantages than known methods, and has a potential wide application prospect.
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Paragraph 0063-0066
(2017/09/26)
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