Reactions of 5-Arylidene-2-thiohydantoins with Halogenated Compounds and Anthranilic Acid

5-arylidene-2-thiohydantoins 1a–c react with ethyl α -chloroacetate 2 and monochloroacetone to give the respective 2-imidazolinones 3a–c and 2-acetonylmercaptohydantoins 9a–c .

Compounds 3a–c react with benzenediazonium chloride to afford hydrazones 5a–c . The reaction of 1a–c with ethylene bromide and with α,α -dichloroacetone gives the respective alkyl mercapto-derivatives 13a–c and 14a–c . The reaction of polyphosphoric acid with 3a–c , 9a–c , 13a–c and 14a–c yields the respective thiazolones 7a–c , imidazothioles 10a–c , imidazo-thiazoles 15a–c and imidazothiazines 16a–c . The mercapto-hydantoins 17a–d react with anthranilic acid to give quinazolin-3,5-diones 19a,b and/or 21a , b . Structural elucidation for the new products are based on compatible elementary and spectroscopic evidences.

Keywords:

• 5-Arylidene-2-thiohydantoins
• anthranilic acid
• dihlogenated compounds
• mono-
• polyphosphoric acid

Notes

*4.1, 4.4 (2t, 4H, SCH ₂-CH ₂Br), 6.2 (s, 1H, Ar-CH═), 7.2–7.5 (m, 5H, Ar-H) and 8.7 (s, 1H, NH, exchangeable with D₂O).

**4.3, 5.4 (2s, 4H, SCH ₂-COCH ₂Cl), 6.2 (s, 1H, Ar-CH=), 7.2–7.5 (m, 5H, Ar-H) and 9.1 (s, 1H, NH, exchangeable with D₂O).

*3.9(s, 3H, OCH ₃), 4.2, 4.6 (2t, 4H, S-CH ₂-CH ₂-N), 6.4 (s, 1H, AR-CH═) and 7.2–7.6 (m, 4H, AR-H).

**3.8 (s, 3H, OCH ₃), 4.2, 4.7 (2s, 2H, 2CH ₂, 6.3 (s, 1H, AR-CH=) and 7.3–7.5 (m, 4H, AR-H).