Reaction of naphthalene-2,3-dicarbaldehyde with cyanide; A unique oxidative condensation product

✍ Scribed by Colin M. Mcgill; Kristian E. Swearingen; Kelly L. Drew; Brian T. Rasley; Thomas K. Green

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2005
• Tongue: English
• Weight: 307 KB
• Volume: 42
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570420401

✦ Synopsis

Naphthalene-2,3-dicarbaldehyde (NDA), a reagent used for the fluorescent detection of amino acids in the presence of cyanide, self-condenses in the presence of cyanide ion and methanol at room temperature to yield a unique crystalline product 2, 15-hydroxybenzo[g]benzo [6,7]isochromeno[4,3-c]isochromen-7(15H)one. The product is proposed to result from facile air oxidation of NDA to a methyl ester in combination with benzoin condensation. Product 2 does not to form in the absence of air. The gHMBC spectrum of 2 distinguishes it from a possible alternative isomeric condensation product.