Stereoselective Synthesis, Crystal Structure and Fungicidal Activity of<i>trans-</i>2,3,6(8)-Trisubstituted-1,3-benzoxazines

唐子龙,; 夏赞稳,; 李新兴,

doi:10.6023/cjoc201508019

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“…Also the results of this paper are consistent with the experimental facts reported. For example, the reduction of compounds containing 4‐OH‐ArCHN structure and other X‐ArCHN structure by NaBH 4 , the former takes longer than the latter under the same reduction conditions, that is, the former is more difficult to be reduced.…”

Section: Resultsmentioning

confidence: 99%

“…For examples, Jia et al employed sodium tetrahydroborate (NaBH 4 ) to reduce the imine CN double bond of ruthenium (II) p ‐cymene complexes containing Schiff‐base ligands [Ru(p‐cymene)LCl] and prepared half‐sandwich ruthenium complexes, which have active catalysts. Tan et al used NaBH 4 to reduce the imine CN double bond in the synthesis of novel 3‐(1,3,4‐thiadiazolyl)‐1,3‐bezoxazines, which have fungicidal activity. Liu et al synthesized 4‐[(5‐aryl‐1,3,4‐thiadiazol‐2‐ylamino)methyl]phenol compounds via the nucleophilic addition reaction of 5‐aryl‐1,3,4‐thiadiazol‐2‐amine with 4‐hydroxybenzaldehyde and the reduction of CN double bond in the presence of NaBH 4 reducing agent.…”

Section: Introductionmentioning

confidence: 99%

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Additional effect of para‐hydroxyl on the reduction potentials of theN‐benzylidenebenzenamines

Cao

Zhou

Cao

2019

J of Physical Organic Chem

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The reduction potential E Red of disubstituted N-benzylidenebenzenamines XArCH NArY (abbreviated as XBAY) is a measure of the electron acceptance ability of the Lowest-energy Unoccupied Molecular Orbital (LUMO) in molecule, which is closely related to the electronic effects of substituents X and Y in molecule. Previous studies on the E Red of XBAY reported by Luo, Wang, and Yuan all did not involve these molecules containing hydroxyl. In this work, 28 samples of disubstituted N-benzylidenebenzenamines containing parahydroxyl, (abbreviated as 4-OHBAY or XBAOH-4 0 ) were synthesized, and their E Red values were measured. Then, 127 compounds were taken as a complicated E Red data set, which involved 28 compounds (4-OHBAY and XBAOH-4 0 ) of this work and 99 compounds XBAY reported by Luo. Based on these data E Red set, through a quantitative regression analysis method and comparison of the factors affecting the E Red , the following results are obtained: (a) Because the phenolic hydroxyl OH can dissociate H + to form phenolic oxygen anion, the change regularity of E Red of compounds 4-OHBAY and XBAOH-4 0 is somewhat different from that of E Red of XBAY compounds without hydroxyl OH. That is, hydroxyl OH has an additional effect on the E Red , which decreases the E Red value. (b) The additional effects of 4-OH on the E Red is different from that of 4 0 -OH. The effect of hydroxyl OH attached to the aldehyde aromatic ring on the E Red is more than that of OH attached to the amine aromatic ring. K E Y W O R D Sadditional effect, para-hydroxyl N-benzylidenebenzenamine, reduction potential, substituent electronic effect

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%