A facile synthesis of 2-aminothiazolo[5,4-b]pyridines and2-aminobanzoxazoles via cyclization of thioureas

Ju Hee Yoon, Hyunmin Song, Sang Wong Kim, Gyoonhee Han, Hea Young Park Choo

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10 Citations (Scopus)

Abstract

2-Aminothiazolo[5,4-b]pyridines and 2-aminobenzoxazoles havebeen synthesized from 2-hydroxy-3-thioureidopyridine and 2-hydroxy-3-thioureidobenzene respectively via acid catalyzed cyclization, which were prepared by the reaction of isothiocyanates with 2-hydroxy-3-aminopyridine or 2-aminophenol. The hydroxyl group of N-(2-hydroxy-5-phenyl)-N′-phenyl thiourea reacted as nucleophile to thioureido carbon to give 2-aminobenzoxazoles, whereas that of N-(2-hydroxypyridino)-N′-phenylthiourea was reacted as leaving group upon nuclephillic sulfur of thiourea group in the presence of trifluoroacetic acid or phosphoric acid.

Original languageEnglish
Pages (from-to)2729-2740
Number of pages12
JournalHeterocycles
Volume65
Issue number11
DOIs
Publication statusPublished - 2005 Nov 1

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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