THIOCYANATION, HALOGENATION, DEHALOGENATION, TRANSHALOGENATION, AND NITRATION OF 2-SUBSTITUTED 4-(2-FURYL)THIAZOLES

Authors

  • Н. О. Салдабол Latvian Institute of Organic Synthesis, Riga LV-1006
  • Ю. Ю. Попелис Latvian Institute of Organic Synthesis, Riga LV-1006
  • В. А. Славинская Latvian Institute of Organic Synthesis, Riga LV-1006

Keywords:

2-R-4-(2-furyl)thiazoles (R = NH2, NHAc, Me), bromination, iodination, nitration, oxidative cleavage of 5-nitro-2-furyl group, transbromination, thiocyanation

Abstract

Bromination and thiocyanation of 2-amino- and 2-acetylamino-4-(2-furyl)thiazoles when 1 mol of reagent is used at 10°C are directed to the 5 position. Formation of 5'-bromo-substituted derivatives when the reaction temperature is raised is the result of a secondary, thermodynamically controlled process. Monohalogenation and mononitration of 4-(2-furyl)-2-methylthiazole are directed to the 5' position. Nitration of 2-acetylamino-4-(5-nitro-2-furyl)thiazole by a nitrating mixture is accompanied by oxidative cleavage of the 5-nitrofuran moiety and leads to formation of 5,5'- and 3',5'-dinitro derivatives.

How to Cite
Saldabol, N. O.; Popelis, J.; Slavinska, V. Chem. Heterocycl. Compd. 2002, 38, 873. [Khim. Geterotsikl. Soedin. 2002, 983.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1020602308595

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Published

2002-07-25

Issue

No. 7 (2002)

Section

Original Papers