Nonbenzenoid aromatic systems. XII. Synthesis of 2-, 3-, and 6-substituted 2-(1-azulyl) ethanols and their tosylate esters

RN McDonald, JM Richmond, JR Curtis…

Index: McDonald,R.N. et al. Journal of Organic Chemistry, 1976 , vol. 41, p. 1811 - 1821

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Citation Number: 36

Abstract

The synthesis of 2-(CH30, CH3, C1, Br, I, CN) and 3-substituted (CH30, CH3, CHsS, Br, COCH3, CN, NOz) derivatives of 2-(l-azulyl) ethanol (l-OH) and 1-OAc by combining conventional procedures are reported. A method for the protodeamination of diethyl 2-amino- 6-bromoazulene-l, 3-dicarboxylate(3) to diethyl 6-bromoazulene-1, 3-dicarboxylate (7) in 93% yield using p-hydroquinone as in situ reducing agent of the intermediate diazonium ...