6502-82-5Relevant articles and documents
Enantioselective Synthesis of (+)-Peganumine A
Piemontesi, Cyril,Wang, Qian,Zhu, Jieping
, p. 11148 - 11151 (2016)
A gram-scale enantioselective total synthesis of (+)-peganumine A was accomplished in 7 steps from commercially available 6-methoxytryptamine. Key steps included (a) a Liebeskind-Srogl cross-coupling; (b) a one-pot construction of the tetracyclic skeleton from an ω-isocyano-γ-oxo-aldehyde via a sequence of an unprecedented C-C bond forming lactamization and a transannular condensation; (c) a one-pot organocatalytic process merging two achiral building blocks into an octacyclic structure via a sequence of enantioselective Pictet-Spengler reaction followed by a transannular cyclization. This last reaction created two spirocycles and a 2,7-diazabicyclo[2.2.1]heptan-3-one unit with excellent control of both the absolute and relative stereochemistry of the two newly created quaternary stereocenters.
Continuous-flow synthesis of thioureas, enabled by aqueous polysulfide solution
ábrányi-Balogh, Péter,Keser?, Gy?rgy M.,Mándity, István M.,Németh, András Gy.,Orsy, Gy?rgy,Szabó, Renáta
supporting information, (2021/06/25)
We have developed the continuous-flow synthesis of thioureas in a multicomponent reaction starting from isocyanides, amidines, or amines and sulfur. The aqueous polysulfide solution enabled the application of sulfur under homogeneous and mild conditions. The crystallized products were isolated by simple filtration after the removal of the co-solvent, and the sulfur retained in the mother liquid. Presenting a wide range of thioureas synthesized by this procedure confirms the utility of the convenient continuous-flow application of sulfur.
Production process of evodiamine and method for recycling solvent in production
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Paragraph 0018; 0042-0044; 0052-0054, (2021/02/24)
The invention relates to the field of organic synthesis, in particular to a production process of evodiamine and a method for recycling a solvent in production. According to the method, tryptamine isadopted as a raw material, evodiamine is obtained through formylation, cyclization and condensation ring closing, phosgene and ethyl chloroformate are prevented from being used in the whole process, the safety risk in the production process is reduced, and the reaction steps are greatly simplified. Meanwhile, a solvent application process in production is realized, so that the production cost is greatly reduced, and the method has an industrial popularization value.
Facile access to: N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones
Huang, Hsin-Yi,Liang, Chien-Fu,Lin, Xiu-Yi,Yen, Shih-Yao
supporting information, p. 5726 - 5733 (2020/08/21)
N-Formamide synthesis using N-formyl imide with primary and secondary amines with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH·H2O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines with TsOH·H2O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole and quinazolinone derivatives. Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- A nd metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation.