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Updated: Jun 5, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
1-[4-(Diamino-methyl-eneamino-sulfon-yl)phenyl-iminiometh-yl]-2-naphtholate N,N-dimethyl-formamide disolvate
Abstract:
The asymmetric unit the title compound, C(18)H(16)N(4)O(3)S·2C(3)H(7)NO, contains a mol-ecule in a zwitterionic form with a deprotonated hydroxyl group and an iminium group, and two dimethyl-formamide solvent mol-ecules. The dihedral angles of the guanidine group and the naphthyl ring system with respect to the central benzene ring are 76.04 (7) and 3.45 (9)°, respectively. The conformation of the mol-ecule may be influenced, in part, by two intra-molecular hydrogen bonds, while in the crystal structure, inter-molecular hydrogen bonds form one-dimensional chains along [010].
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The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
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