Heterocylic Synthesis by Persulphate Oxidation.
Final technical rept. 1 Nov 73-31 Oct 74,
ABERDEEN UNIV (SCOTLAND) DEPT OF CHEMISTRY
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The reaction of thionyl chloride with 2-carboxyisopropoxyazobenzenes gives 4-o-chloroanilinobenzoxazin-3-ones in good yield. Persulphate oxidation of a series of oximino-O-acetic acids derived from o-phenylbenzophenone, o-phenylacetophenone, and o-phenylbenzaldehyde gave phenanthridines in good yield. Persulphate oxidation of 2-alkylamino-3-phenyl-1,4-naphthoquinones in aqueous acetonitrile yields benzobcarbazole-6,11-diones by radical cyclisation. 2-Arylamino anilino, o-toluidino analogues also undergo radical coupling to form N,N-di3-phenyl-1,4-naphthoquinon-2-ylbenzidines. Mechanisms are discussed.
- Organic Chemistry