Efficient Microwave-Assisted Synthesis of 5-Deazaflavine Derivatives.docVIP

Molecules 2010, 15, 7227-7234; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Efficient Microwave-Assisted Synthesis of 5-Deazaflavine Derivatives Jorge Trilleras 1,*, Luis Gabriel López 1, Dency José Pacheco 1, Jairo Quiroga 2,*, Manuel Nogueras 3,*, José M. de la Torre 3 and Justo Cobo 3 1 Grupo de Investigación en Compuestos Heterocíclicos, Programa de Química, Facultad de Ciencias Básicas, Universidad del Atlántico, A.A.1890 Barranquilla, Colombia 2 Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360 Cali, Colombia 3 Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain * Author to whom correspondence should be addressed; E-Mails: jaiquir@.co (J.Q.); jorgetrilleras@.co (J.T.); mmontiel@ujaen.es (M.N.). Received: 16 September 2010; in revised form: 30 September 2010 / Accepted: 3 October2010 / Published: 20 October 2010 Abstract: A series of pyrimido[4,5-b]quinolines (5-deazaflavines), were synthesized by microwave assisted intramolecular cyclization. The N4-substituted-2,4-diamino-6-chloro- pyrimidine-5-carbaldehydes, were prepared by selective monoamination of 2-amino-4,6- dichloropyrimidine-5-carbaldehyde with aliphatic and aromatic amines. Keywords: pyrimidoquinolines; cyclocondensation; microwave; deazaflavines 1. Introduction The 5-deazaflavine (pyrimido[4,5-b]quinoline) ring system I is of great interest because of its structural similarity to the pyrimido[4,5-b]quinoxaline ring system of the naturally-occurring flavines (II, Figure 1), with N-5 being replaced by CH and thus keeping the redox properties of I quite similar to those of compounds II. Surprisingly, not much has been reported on the synthesis and properties of pyrimido[4,5-b]quinolines. Flavo-enzymes require flavine mononucleotide (FMN) or flavine adenine dinucleotide (FAD) as a coenzyme and catalyze o