New Reactivities of Nitrogen-Containing Aromatics and Their Synthetic Application

• Published in: YAKUGAKU ZASSHI Vol. 122; no. 11; pp. 869 - 888
• Main Author: MURAKAMI, Yasuoki
• Format: Journal Article
• Language: Japanese
• Published: Japan The Pharmaceutical Society of Japan 01.11.2002
• Subjects: Acylation; Aniline Compounds - chemical synthesis; Ar-N chirality; Catalysis; diacylanilines; Ergot Alkaloids - chemical synthesis; Fischer indole synthesis; indoles; Indoles - chemical synthesis; Nitrogen; Palladium; Pd-catalyzed reaction; Pyrroles
• ISSN: 0031-6903; 1347-5231
• DOI: 10.1248/yakushi.122.869

This review describes new knowledge on reactivities and syntheses of N-containing aromatics and their application to the synthesis of natural products covering three subjects. 1) The first part describes the Fischer indole synthesis of o-substituted phenylhydrazones, its mechanism, Reissert indole synthesis, a new synthetic approach from pyrrole to indole, some reactions of indoles (i.e., etc.), acylation, bromination, debromination, debenzylation, Vilsmeier-Haack reaction, and synthesis of 4-methoxy-β-carboline alkaloids. 2) The second part describes a new method of introduction of allyl and vinyl groups on the indole nucleus by means of a Pd catalyst. This method was applied to the synthesis of optically active ergot alkaloids. 3) The third part describes the synthesis of o-substituted diacylanilines and its application to chemoselective acylating reagents. A study on axial chirality based on the Ar-N axis is also involved.