4815-99-0Relevant articles and documents
Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide-Dimethyl Sulfoxide
Sang, Dayong,Tian, Juan,Tu, Xiaodong,He, Zhoujun,Yao, Ming
, p. 704 - 712 (2019/01/23)
Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o -hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.
Ether bond cracking method of phenylalkyl ether
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Paragraph 0117-0119, (2018/11/26)
The invention discloses an ether bond cracking method of phenylalkyl ether. The method comprises the following steps: performing ether bond breaking reaction on phenylalkyl ether at -20 to reflux temperature in the presence of aluminium triiodide and dimethyl sulfoxide, thereby generating phenol and derivatives thereof. The method disclosed by the invention is mild in condition, simple and convenient for operation, high in yield, and extensive in applicable phenylalkyl ether range.
Carbodiimides as Acid Scavengers in Aluminum Triiodide Induced Cleavage of Alkyl Aryl Ethers
Sang, Dayong,Wang, Jiahui,Zheng, Yun,He, Jianyuan,Yuan, Caili,An, Qing,Tian, Juan
, p. 2721 - 2726 (2017/06/13)
A practical procedure for the cleavage of alkyl aryl ethers containing labile functional groups has been developed using aluminum triiodide as the ether cleaving reagent. Carbodiimides, typically used as dehydration reagents for the coupling of amines and carboxylic acids to yield amide bonds, are found to be effective hydrogen iodide scavengers that prevent acid-labile groups from deterioration. The method is applicable to variant alkyl aryl ethers such as eugenol, vanillin, ortho -vanillin and methyl eugenol. Suitable substrates are not limited to alkyl o -hydroxyphenyl ethers.
Pyridine Improves Aluminum Triiodide Induced Selective Cleavage of Alkyl o -Hydroxyphenyl Ethers: A Practical and Efficient Procedure for the Preparation of Hydroxychavicol by Demethylation of Eugenol
Sang, Dayong,Yao, Ming,Tian, Juan,Chen, Xiaoman,Li, Li,Zhan, Hongju,You, Linhong
, p. 138 - 142 (2016/12/26)
Demethylation of eugenol with aluminum triiodide is complicated by an unexpected hydrogenation side reaction. The hydrogenation proceeds through a cascade deprotonation, hydroiodination, and hydrogen-halogen exchange process, and can be prevented by suppressing the hydroiodination in advance. A practical demethylation procedure is thus developed that delivers hydryoxychavicol in essentially quantitative yield by using pyridine as an additive. The method is selective towards cleaving alkyl o-hydroxyphenyl ethers and is compatible with a variety of functional groups.
Ether bond rupturing method for ortho-hydroxyl phenyl alkyl ether
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Paragraph 0083; 0084; 0085; 0086; 0087, (2017/05/27)
The invention discloses an ether bond rupturing method for ortho-hydroxyl phenyl alkyl ether. The method comprises the following steps that in a solvent, an ether bond rupturing reaction occurs to ortho-hydroxyl aryl alky ether at the temperature ranging from minus 20 DEG C to the catalyst reflux temperature under the existence of alkali and a catalyst aluminum triiodide, and catechol and derivatives thereof are generated. The method is simple, reaction conditions are simple, and operation is easy; besides, the yield is high, and the applicable ortho-hydroxyl phenyl alkyl ether range is wide.
Ether bond breakage method for phenylalkyl ethers
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Paragraph 0148-0150, (2017/07/19)
The invention discloses an ether bond breakage method for phenylalkyl ethers. The method comprises the step: subjecting the phenylalkyl ethers to an ether bond breakage reaction at the temperature of -20 DEG C to reflux temperature in an organic solvent in the presence of aluminum triiodide and carbodiimide, so as to produce phenols and derivatives thereof. The method is moderate in conditions, simple and convenient in operation, high in yield and wide in applicable phenylalkyl ether range.
cGAS ANTAGONIST COMPOUNDS
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Paragraph 0403, (2017/11/06)
Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.
Total synthesis of altenusin and alterlactone
Cudaj, Judith,Podlech, Joachim
supporting information; experimental part, p. 371 - 374 (2012/03/27)
The resorcylic lactone alterlactone, a mycotoxin produced by alternaria sp., was synthesized for the first time. The total synthesis was achieved in nine steps with 69% yield starting with acetal-protected phloroglucinic acid and 6-bromopiperonal, where t
Synthesis of Ring-Alkylated Isoproterenol Derivatives
Reitz, Allen,Avery, Mitchell A.,Verlander, Michael S.,Goodman, Murray
, p. 4859 - 4863 (2007/10/02)
2-Propyl-, 5-propyl-, and 6-propylisoproterenols (2a, 2b, and 1d, respectively) have been synthesized as models for polymer drug conjugates.Key intermediates were the propenylbenzaldehydes 3a-c.The (isopropylamino)phenethanol side chain was constructed fr
