- Convenient synthesis of 2-Amino-4H-chromenes from photochemically generated o-quinone methides and malononitrile
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2-Amino-4H-chromenes were synthesized in moderate to good yields by the reaction of o-quinone methides photochemically generated from o-(dimethylaminomethyl)phenols with malononitrile. This method was applicable to the synthesis of fluorinated chromenes that were difficult to obtain by other methods. In addition, o-(hydroxymethyl)phenols could be used for the reaction in the presence of tertiary amine bases.
- Fujiwara, Makoto,Sakamoto, Masanori,Komeyama, Kimihiro,Yoshida, Hiroto,Takaki, Ken
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- Oxidative ortho-amino-methylation of phenols via C-H and C-C bond cleavage
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Initiated by CCl3Br, phenols undergo efficient ortho-selective oxidative cross dehydrogenative coupling (CDC) with trimethylamine. When tetramethylethylenediamine (TMEDA) is used instead of trimethylamine, oxidative carbon-carbon activation coupling (CAC) could occur to give the same salicylamines together with CDC by-products. These reactions are accelerated by a gold salt.
- Sun, Wenbo,Lin, Huacan,Zhou, Wenyu,Li, Zigang
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p. 7491 - 7494
(2014/02/14)
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- Synthesis of substituted salicylamines and dihydro-2H-1,3-benzoxazines
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Phenols were converted to their magnesium salts with the MgCl2-Et3N base system and subsequently reacted with Eschenmoser's salt, affording N,N-dimethyl substituted benzylamines in high to excellent yields. A series of mono N-substituted benzylamines were prepared in one-pot syntheses by ortho-formylation of phenols to corresponding salicylaldehydes, which in turn reacted with amines to imines. The imines were subsequently reduced to mono N-substituted benzylamines. Some of these benzylamines were further converted, without work-up, to mono N-substituted dihydro-2H-1,3-benzoxazines.
- Anwar, Hany F.,Skatteb?l, Lars,Hansen, Trond Vidar
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p. 9997 - 10002
(2008/02/13)
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