Revisiting the Reaction Between Diaminomaleonitrile and Aromatic Aldehydes a Green Chemistry Approach 英文参考文献.docVIP

Molecules 2006, 11, 858-866 molecules ISSN 1420-3049 Full Paper Revisiting the Reaction Between Diaminomaleonitrile and Aromatic Aldehydes: a Green Chemistry Approach Augusto Rivera 1,*, Jaime Ríos-Motta 1 and Francisco León 2 1 Departamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, Carrera 30 # 45-03, Bogotá-D.C., Colombia. Tel.: (+57)-1-3165000; Fax: (+57)-1-3165220. 2 Instituto Universitario de Bio-Orgánica-Instituto de Productos Naturales y Agrobiología, Avenida Astrofísico Francisco Sánchez, 2, 38206, La Laguna, Tenerife, Spain * Author to whom correspondence should be addressed. E-mail: ariverau@.co Received: 13 September 2006; in revised form: 9 October 2006 / Accepted: 10 October 2006 / Published: 11 November 2006 Abstract: The reaction between diaminomaleonitrile (DAMN) and aldehydes and the resulting monoimines are well known. Since the standard reaction conditions involve the use of toxic solvents (typically methanol), we have sought to apply green chemistry principles to this reaction by either using water as the solvent without any catalysts or employing “solvent-free” conditions. The monoimines derived from DAMN are of interest as precursors for obtaining different heterocyclic systems and linear polymers. The methodologies used have significant advantages with regards to cost and environmental considerations. Keywords: DAMN, monoimines, Green Chemistry, aromatic aldehydes. Introduction Tetrameric HCN (diaminomaleonitrile, DAMN) is one of the most versatile reagents in Organic Chemistry. It has been used as a precursor for producing nucleotides and for synthesising a wide variety of heterocyclic compounds [1] including purines [2,3], pyrimidines [4], pyrazines [5] (some which are widely employed in the fluorescent dye industry [6]), imidazoles [7], biphenylenes [8], porphyrazines (which have great potential in optical sens