L-Proline-catalysed sequential four-component "on water" protocol for the synthesis of structurally complex heterocyclic ortho-quinones

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 13; no. 11; pp. 3248 - 3254
• Main Authors: Rajesh, Stephen Michael, Bala, Balasubramanian Devi, Perumal, Subbu, Carlos Menendez, J.
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 01.01.2011; Royal Society of Chemistry
• Subjects: Catalysis; Chemistry; Chemistry, Multidisciplinary; Exact sciences and technology; General and physical chemistry; Green & Sustainable Science & Technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Noncondensed benzenic compounds; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Science & Technology - Other Topics; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; ANTIMYCOBACTERIAL ACTIVITY; MULTICOMPONENT REACTIONS; ORGANIC-SYNTHESIS; KETONES; DIVERSITY-ORIENTED SYNTHESIS; CASCADE REACTIONS; DIELS-ALDER REACTIONS; VERSATILE CATALYST; 3-COMPONENT DOMINO PROTOCOL; FACILE; Water; Catalytic reaction; Purification; Multicomponent reaction; Nitrogen heterocycle; Quinone; Benzaldehyde; Proline; Diketone; Complexes; Naphthalene derivatives; α-Aminoacid; Sequential; Aminoacid; Preparation; Reaction time; Benzenic compound; Aromatic compound; Extraction; Aryl; Chemical synthesis; Atom economy; Benzaldehyde derivatives; Successive reaction
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c1gc15794a

The L-proline-catalyzed synthesis of 7-(aryl)-8-methyl-10-phenyl-5H-benzo[h]pyrazolo[3,4-b]quinoline-5,6(10H)-diones via the four-component sequential reaction of phenylhydrazine, 3-aminocrotononitrile, substituted benzaldehydes and 2-hydroxynaphthalene-1,4-dione is described. This "on water" protocol proceeds in high atom economy and leads to the generation of two rings, together with two C-C, one C-N and two C=N bonds in a single operation. The environmental advantages of the method include short reaction time, excellent yield, easy work-up, and the absence of extraction and chromatographic purification steps.