Month 2018 Synthesis and Reactions of New Thiazoles and Pyrimidines Containing Sulfonate Moiety A. Khodairy, Ali M. Ali,* and M.T. El-Wassimy Department of Chemistry, Faculty of Science, Sohag University, Sohag, 82524, Egypt * E-mail: elssan@yahoo.com Received October 2, 2017 DOI 10.1002/jhet.3126 Published online 00 Month 2018 in Wiley Online Library (wileyonlinelibrary.com). Treatment of 2-tosyloxybenzylidinethiosemicarbazone (2) with active halo compounds afforded thiazoles 3–5. Moreover, reaction of compound 2 with acetic anhydride or dimethylformamide dimethylacetal gave N,N diacetyl 6 and dimethylamino derivatives 7, respectively. Cyclization of thiazole derivatives 3 with some arylidenemalononitriles yielded thiazolo[2,3-d]pyrans 8–12. Multicomponent reaction of 2-tosyloxybenzaldehyde (1) with urea, thiourea, or compound 2 and ethyl acetoacetate or acetylacetone afforded pyrimidines 13–14. The structures of compounds were elucidated by elemental and spectral analyses. J. Heterocyclic Chem., 00, 00 (2018). INTRODUCTION Thiazole and pyrimidine derivatives exhibited range of pharmacological and biological activities such as antimicrobial [1–4], anti-inflammatory [5–7], antipyretic [8,9], antiviral [10,11], antimicrobial [12–14], antifungal [14,15], anticancer [16–18], antiarrhythmics, and antidepressants [6,7]. Heterocyclic compounds that contain sulfonate moiety have received considerable attention during the last two decades as they are endowed with variety of biological activities such as papillomavirus microbicidal [19], antineoplastic [20], anticancer activity [21–23], and anti-human immunodeficiency virus 1 [24]. Therefore, in view of these observations and in conjunction with our previous interest in synthesis of new heterocyclic compounds [25–29], the present research deals with synthesis of novel thiazole and pyrimidine derivatives. RESULTS AND DISCUSSION Our synthesis begin with the reaction of 2- tosyloxybenzaldehyde 1 [30] with thiosemicarbazide in methanol under reflux in presence of TEA to yield 2- tosyloxybenzylidenethiosemicarbazone 2 (Eq. 1). (1) Infrared (IR) spectrum of compound 2 revealed disappearance of an absorption band of the CHO group and appearance of new bands at 3303, 3210, and 3157 cm À1 corresponding to NH 2 and NH groups. 1 H NMR spectrum (δ, DMSO-d 6 ) showed exchangeable singlet signal due to NH group at 11.48 ppm, N═CH group at 8.26 ppm, aromatic proton signals in the range 8.26–7.13 ppm consistent with NH 2 group, and methyl group at 2.41 ppm, respectively. Treatment of compound 2 with respective halo reagent, such as ethyl bromoacetate, phenacyl bromide, or chloroacetonitrile gave thiazole derivatives 3–5, respectively (Scheme 1). © 2018 Wiley Periodicals, Inc.