The cyclodesulphurization of thio-compounds. Part 15: Synthesis of 6-substituted aminophenanthridines from some thiourea derivatives.
Several N-alkyl, aryl, and aralkyl-N'-2-biphenylthiourea derivatives have been synthesized and cyclodesulphurized into the corresponding 6-substituted aminophenanthridines. The ring closure was brought about with mercuric chloride, phosphoryl chloride or polyphosphoric acid. Phosphoryl chloride was found to be the most efficient in inducing ring closure and producing the highest yield of cyclized products. The results of study on the cyclodesulphurization reaction mechanism suggested the formation of a carbodiimide intermediate and identified some of the organic mercurials involved in the various stages of the reaction.
D003500:Cyclization; D008628:Mercury; D008722:Methods; D010617:Phenanthridines / Q000138:chemical synthesis*; D013890:Thiourea / Q000031:analogs & derivatives*
D010617:Phenanthridines; D008628:Mercury; D013890:Thiourea