- REDUCTION OF 1-(3,5-DI-TERT-BUTYL-2-HYDROXYPHENYL)PYRIDINIUM HALIDES WITH RANEY Ni-AL ALLOY IN AN ALKALINE SOLUTION AFFORDING 2,4-DI-TERT-BUTYLBENZOXAZOLO-5a,6,7,9,10-HEXAHYDROPYRIDINES
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Treatment of 1-(3,5-di-tert-butyl-2-hydroxyphenyl)pyridinium halides (1a-1c) with Raney Ni-Al alloy in an alkaline solution afforded the corresponding 2,4-di-tert-butylbenzoxazolo-5a,6,7,8,9,10-hexahydropyridines (4a-4c).In the case of 1b, 2,4-di-t
- Fukata, Gouki,Itoh, Takashi,Tashiro, Masashi
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- METHOD FOR PRODUCING AN ARENE WITH AN AROMATIC C-N BOND ORTHO TO AN AROMATIC C-O BOND
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A method for producing an arene with an aromatic C—N bond ortho to an aromatic C—O bond from a hydroxy arene comprising said aromatic C—O bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a C—N bond ortho to a C—O bond of Formula (Va) and (Vb), respectively:
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Paragraph 0429; 0431; 0432
(2017/03/28)
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- Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines
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By using o-benzoquinone as an internal oxidant, the regio- and diastereoselective functionalization of the secondary over the tertiary α-C-H bond of 2-substituted pyrrolidines is first realized. Subsequent intermolecular addition of a nucleophile to the g
- Cheng, Yong-Feng,Rong, Hao-Jie,Yi, Cheng-Bo,Yao, Jun-Jun,Qu, Jin
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supporting information
p. 4758 - 4761
(2015/10/12)
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- Interaction of 3,5-di-tert-butyl-o-benzoquinone with secondary amines - A pathway to new sterically hindered N,N-disubstituted o-aminophenols
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The interaction of 3,5-di-tert-butyl-o-benzoquinone with secondary amines has been studied. The synthetic procedure was developed in order to synthesize a series of new N,N-disubstituted o-aminophenols. The interaction of 3,5-di-tert-butyl-o-benzoquinone
- Cherkasov, Vladimir,Druzhkov, Nikolay,Kocherova, Tatiana,Fukin, Georgii,Shavyrin, Andrey
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experimental part
p. 80 - 84
(2011/02/28)
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- Reduction of 1-(2-Hydroxy-3,5-di-t-butylphenyl)pyridinium Halides and Their Zwitterions. Formation of Di- and Tetra-hydropyridobenzoxazoles
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Reduction of 1-(2-hydroxy-3,5-di-t-butylphenyl)pyridinium halides (1a-d) and/or their zwitterions (2a-d) with Raney Ni-Al alloy, Raney Ni (W2) and NaBH4 were investigated.When (1) was treated with Ni-Al alloy in a mixture of methanol and 30percent aqueous
- Fukata, Gouki,Itoh, Takashi,Mataka, Shuntaro,Tashiro, Masashi
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p. 327 - 332
(2007/10/02)
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- Cyclodienones. 7. Preparation and Reduction of 1-(3,5-Di-tert-butyl-2-hydroxyphenyl)pyridinium Halides
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The reactions of 4-bromo- (1a) and 4-chloro-2,4,6-tri-tert-butyl-2,5-cyclohexadien-1-one (1b) with compounds such as pyridine (4a), α- (4b), β- (4c), and γ-picoline (4d), and 3,5-lutidine (4e) were carried out under various conditions to produce the corresponding 1-(3,5-di-tert-butyl-2-hydroxyphenyl)pyridinium halides (7) or their intramolecular salts (8).The reduction of 7 and 8 with NaBH4 in methanol afforded in good yields the corresponding tetrahydropyridine derivatives (21), which were reduced to o-piperidinophenols (22) by hydrogenation with Raney Ni (W2) catalyst in high yields.The reaction pathway of the formation of 7 is also discussed.
- Fukata, Gouki,Itoh, Takashi,Tashiro, Masashi
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p. 4454 - 4458
(2007/10/02)
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