Facile and Convenient Synthetic Methods for Fluorine-Containing Benzo[c]thioxanthenes and Benzo[c]xanthenes from N,N-Dimethyl-1-naphthylamine

Etsuji Okada; Ryoichi Masuda; Masaru Hojo; Naonori Imazaki; Koichi Takahashi

doi:10.1055/s-1992-26156

Synthesis 1992; 1992(6): 536-538
DOI: 10.1055/s-1992-26156

short paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Facile and Convenient Synthetic Methods for Fluorine-Containing Benzo[c]thioxanthenes and Benzo[c]xanthenes from N,N-Dimethyl-1-naphthylamine

Etsuji Okada^* , Ryoichi Masuda, Masaru Hojo, Naonori Imazaki, Koichi Takahashi

^*Department of Industrial Chemistry, Faculty of Engineering, Kobe University, Kobe 657, Japan

Abstract

PDF Download All articles of this category

Aromatic nucleophilic N-S and N-O exchange reactions of N,N-dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine (1) with thiophenols and phenols gave the corresponding 2,4-bis(trifluoroacetyl)-1-(arylthio)naphthalenes 2 and -1-(4-methoxyphenoxy)naphthalene (5) in moderate to excellent yields. Acid-catalyzed cyclization reactions of 2 and 5 afforded fluorine-containing 7H-benzo[c]thioxanthenes 3,4 and 7H-benzo[c]xanthenes 6,7, respectively, in high yields.

PDF (242 kb)