- Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines by Two Tandem SNAr Events. Part 2 – The Use of o-[N-(Hetero)aryl]aminomethyl Phenols
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As was anticipated based on mechanistic reasoning, bis-nucleophilic o-(arylamino)methyl phenols underwent a facile, base-promoted cyclocondensation with reactivity matched bis-electrophilic (hetero)aromatic substrates to give a rare type of substituted di
- Firsov, Andrey,Sapegin, Alexander,Krasavin, Mikhail
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- Screening of simple carbohydrates as a renewable organocatalyst for the efficient construction of 1,3-benzoxazine scaffold
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A convenient protocol for the two component preparation of 1,3-benzoxazines by using several protected and unprotected carbohydrate molecules as organocatalysts have been developed which is broadly applicable to condensation reaction between variety of Ma
- Y?ld?r?m, Ayhan,Kaya, Yunus,G?ker, Mustafa
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- Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations
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Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.
- Cettolin, Mattia,Bai, Xishan,Lübken, Dennis,Gatti, Marco,Facchini, Sofia Vailati,Piarulli, Umberto,Pignataro, Luca,Gennari, Cesare
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p. 647 - 654
(2018/10/24)
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- Metal-Free Diaryl Etherification of Tertiary Amines by Ortho-C(sp2)-H Functionalization for Synthesis of Dibenzoxazepines and -ones
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A phenyliodine(III) diacetate mediated umpolung reactivity of the tertiary amines with suitably substituted o-hydroxybenzyl and phenyl groups is exploited to facilitate o-C(sp2)-H functionalization to afford diaryl ethers. The presence of an o-
- Jamsheena, Vellekkatt,Mahesha, Chikkagundagal K.,Joy, M. Nibin,Lankalapalli, Ravi S.
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supporting information
p. 6614 - 6617
(2017/12/26)
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- Efficient synthesis of 2,3-disubstituted-1,3-benzoxazines by chlorotrimethylsilane-mediated aza-acetalizations of aromatic aldehydes
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A series of novel substituted 3,4-dihydro-2H-1,3-benzoxazines were prepared in moderate to good yields by aza-acetalizations of aromatic aldehydes with 2-(N-substituted aminomethyl)phenols in the presence of chlorotrimethylsilane or SnCl4. It w
- Tang, Zilong,Zhu, Zhonghua,Yan, Lin,Chang, Shuhong,Liu, Hanwen
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p. 1116 - 1120
(2013/10/21)
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- SnCl4-catalyzed aza-acetalization of aromatic aldehydes: Synthesis of aryl substituted 3,4-dihydro-2H-1,3-benzoxazines
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Stannic tetrachloride was an efficient Lewis acid catalyst for the aza-acetalization of aromatic aldehydes with o-arylaminomethyl phenols, and a series of novel aryl substituted 3,4-dihydro-2H-1,3-benzoxazines were prepared in good yields under mild condi
- Tang, Zilong,Chen, Weiwen,Zhu, Zhonghua,Liu, Hanwen
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scheme or table
p. 1372 - 1383
(2012/04/04)
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- Synthesis and fungicidal activity of novel 2,3-disubstituted-1,3- benzoxazines
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A series of new 2,3-disubstituted-3,4-dihydro-2H-1,3-benzoxazines were prepared in moderate to excellent yields by aza-acetalizations of aromatic aldehydes with 2-(N-substituted aminomethyl)phenols in the presence of TMSCl. Their structures were confirmed
- Tang, Zilong,Zhu, Zhonghua,Xia, Zanwen,Liu, Hanwen,Chen, Jinwen,Xiao, Wenjing,Ou, Xiaoming
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scheme or table
p. 8174 - 8185
(2012/09/25)
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- Mild and rapid method for the generation of ortho -(naphtho)quinone methide intermediates
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A new mild method has been devised for generating o-(naphtho)quinone methides via fluoride-induced desilylation of silyl derivatives of o-hydroxybenzyl(or 1-naphthylmethyl) nitrate. The reactive o-(naphtho)quinone methide intermediates were trapped by C,
- Shaikh, Abdul Kadar,Cobb, Alexander J. A.,Varvounis, George
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p. 584 - 587
(2012/03/10)
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- Synthesis of 2,3-diaryl-3,4-dihydro-2H-1,3-benzoxazines and their fungicidal activities
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A series of novel 2,3-diaryl-3,4-dihydro-2H-1,3-benzoxazines have been prepared in high yields from o-arylaminomethylphenols and aromatic aldehydes in the presence of SnCl4 for the first time, and their fungicidal activities were investigated t
- Tang, Zilong,Chen, Weiwen,Zhu, Zhonghua,Liu, Hanwen
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scheme or table
p. 255 - 260
(2011/06/19)
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- Synthesis and structure-antibacterial activity relationship studies of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones
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The synthesis and characterization of a series of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin- 3(2H)-thiones were presented. Preliminary in vitro antimicrobial activity of the compounds was assessed against a panel of microorganisms including S.
- Agirbas, Hikmet,Kemal, Berat,Budak, Fatma
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experimental part
p. 1170 - 1180
(2012/05/05)
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- Synthesis of substituted 1,4-benzoxazepin-3-one derivatives
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A synthesis of substituted 1,4-benzoxazepin-3-one is described starting from salicylaldehyde, aniline and chloroacetyl chloride. Use of 2-bromo-3-phenylpropionyl chloride gave access to 2-benzyl-1,4-benzoxazepin-3-one; an addition/elimination sequence afforded the corresponding benzylidene derivative which structure has been confirmed by an X-Ray analysis. Biphenyl substituents were also introduced in position -4 of this scaffold.
- Davion, Yann,Guillaumet, Gérald,Léger, Jean-Michel,Jarry, Christian,Lesur, Brigitte,Mérour, Jean-Yves
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p. 1093 - 1112
(2007/10/03)
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- Synthesis of 5-(4-aryl)-2-phenyl-5,6-dihydrobenzo[bl[1,5]oxazocin-4-ones
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Cyclization of N-aryl-N-(2-hydroxybenzyl)-3-phenylpropynamide in basic medium under the influence of a catalytic amount of Pd(0) afforded the eight-membered framework 5-(4-aryl)-2-phenyl-5,6-dihydrobenzo[b][1,5]-oxazocin-4-ones.
- Davion, Yann,Guillaumet, Ge?rald,Le?ger, Jean-Michel,Jarry, Christian,Lesur, Brigitte,Me?rour, Jean-Yves
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p. 1793 - 1804
(2007/10/03)
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- Qualitative analysis of the stability of the oxazine ring of various benzoxazine and pyridooxazine derivatives with proton nuclear magnetic resonance spectroscopy
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A series of 3,4-dihydro-1,3-benzoxazine and 3,4-dihydro-1,3-pyridooxazine derivatives was synthesized, and the hydrolysis of the derivatives was studied with proton nuclear magnetic resonance spectroscopy. The oxazine derivatives underwent various degrees of hydrolysis when H2O was added to dimethyl sulfoxide solutions of the compounds. The rates and extents of decomposition of the oxazine ring systems depended on the electronic effects of substituents within the molecules. Examination of the proton nuclear magnetic resonance spectra that were generated during decomposition of the oxazines and trends in stability of the oxazine derivatives suggest the formation of an intermediate in the hydrolysis mechanism.
- Moloney,Craik,Iskander
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p. 692 - 697
(2007/10/02)
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- New Route for the Preparation of 2H-3-Aryl-3,4-dihydro-1,3-benzoxazines and 2H-3-Aryl-3,4-dihydro-4-methyl-1,3-benzoxazines
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2-Hydroxybenzaldehyde (1) and 1-(2-hydroxyphenyl)ethanone (2) on reaction with different primary aromatic amines gave 2-(arylimino)methylphenols (3) and 2-phenols (4), respectively. 3 and 4 on reduction with sodium borohydride gave 2-(arylamino)methylphenols (5) and 2-phenols (6), which underwent cyclisation with formaldehyde to form 2H-3-aryl-3,4-dihydro-1,3-benzoxazines (7) and 2H-3-aryl-3,4-dihydro-4-methyl-1,3-benzoxazines (8), respectively.
- Joglekar, S. J.,Samant, S. D.
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p. 110 - 111
(2007/10/02)
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- THERMAL DECOMPOSITION OF 2-HYDROXYBENZYLAMINES
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The results are given of the preparation of a number of 2-hydroxybenzylamines and their thermal decomposition.The thermolysis reactions and the formation of the corresponding amines take place smoothly and with good yields.
- Vinogradova, V. I.,Yunusov, M. S.
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p. 308 - 311
(2007/10/02)
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