Cerium(IV) Ammonium Nitrate Is an Excellent, General Catalyst for the Friedlander and Friedlander-Borsche Quinoline Syntheses: Very Efficient Access to the Antitumor Alkaloid Luotonin A

• Published in: Journal of organic chemistry Vol. 74; no. 15; pp. 5715 - 5718
• Main Authors: Sridharan, Vellaisamy, Ribelles, Pascual, Teresa Ramos, Ma, Carlos Menendez, J.
• Format: Journal Article
• Language: English
• Published: WASHINGTON Amer Chemical Soc 07.08.2009; American Chemical Society
• Subjects: Alkaloids - chemical synthesis; Alkaloids - chemistry; Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Biological and medical sciences; Catalysis; Catalysts: preparations and properties; Cerium - chemistry; Chemistry; Chemistry, Organic; Exact sciences and technology; General and physical chemistry; General aspects; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Medical sciences; Molecular Structure; Nitrates - chemistry; Organic chemistry; Pharmacology. Drug treatments; Physical Sciences; Preparations and properties; Pyrroles - chemical synthesis; Pyrroles - chemistry; Quinones - chemical synthesis; Quinones - chemistry; Science & Technology; Stereoisomerism; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; MILD; OMICRON-AMINOBENZALDEHYDE; ACID; SOLVENT-FREE CONDITIONS; ANNULATION; 3-COMPONENT REACTION; DERIVATIVES; ACRIDONE ALKALOIDS; HIGHLY EFFICIENT; GREEN APPROACH; Antineoplastic agent; Alkaloid; Condensation reaction; Chemical reagent; Friedlaender synthesis; Nitrogen heterocycle; Quinoline derivatives; Chemical synthesis; Acid medium; Catalyst
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo900965f

The use of cerium(IV) ammonium nitrate as a catalyst of the Friedlander reaction allows the synthesis of polysubstituted quinoline derivatives in excellent yields, avoiding the traditional harshly basic or acidic conditions. Unlike most other previously known reagents, CAN allows double condensations and is also an excellent catalyst for the Borsche variation of the Friedlander reaction, which has been applied to the very efficient synthesis of the antitumor alkaloid luotonin A.