Synthesis of substituted anilines via a gold-catalyzed three-component reaction
Hirofumi Ueda1, Ryota Yamamoto1, Minami Yamaguchi1
1Graduate School of Pharmaceutical Sciences, Tohoku University Aoba 6-3, Aramaki, Aoba-ku, Sendai, Miyagi 980-8578, Japan. tokuyama@mail.pharm.tohoku.ac.jp.
Abstract:
A three-component reaction for the synthesis of substituted anilines by a gold(i)-catalyzed domino reaction was developed. Cationic gold catalysts selectively and sequentially activated two different alkynes, which were involved in pyrrole synthesis and subsequent Diels-Alder reaction. The sequential formal (3 + 2) annulation/Diels-Alder reaction of three components provided a variety of substituted anilines in a modular fashion. Moreover, utility of the aniline products was demonstrated by derivatization to substituted benzoxazines, which are pharmaceutically important heterocycles.
Related Concept Videos
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...


