One pot synthesis of 5,10-dihydrophenazine compounds and 5,10-substituted dihydrophenazines

US6242602A · kind A · utility

Assignee

• GENTEX CORPORATION · US

Inventors

• Punam Giri · Holland, US
• Harlan J. Byker · Holland, US
• Kelvin L. Baumann · Holland, US

Key dates

• Filing date: Mar 29, 1999
• Grant date: Jun 5, 2001
• Expiry date: Mar 29, 2019

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D241/46
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Dihydrophenazines and bis(dihydrophenazines) are prepared in high yield under commercially viable reaction conditions by reacting a catechol with a 1,2-diaminoaryl compound, wherein either the catechol or the 1,2-diaminoaryl compound is provided in at least 50% molar stoichiometric excess. The product may be oxidized to the corresponding phenazine, but is preferably derivatized at one or both of the 5,10-positions to form a monosubstituted or disubstituted dihydrophenazine or bis(dihydrophenazine). Most preferably, 5,10-dialkyl-5,10-dihydrophenazines are prepared starting from catechol and 1,2-diaminoaryl compound in a one pot synthesis. The products are useful as dyes, and in particular as chromophores in electrochromic systems.