809231-02-5Relevant articles and documents
Preparation method of arylamine o-substituted compound
-
Paragraph 0080-0082, (2019/11/13)
The invention discloses a preparation method of an arylamine o-substituted compound as shown in a formula I in the specification. The preparation method provided by the invention comprises the following steps: (1) in a continuous flow reactor, carrying ou
Indole synthesis by controlled carbolithiation of o-aminostyrenes
Kessler, Albane,Coleman, Claire M.,Charoenying, Patchanee,O'Shea, Donal F.
, p. 7836 - 7846 (2007/10/03)
An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.