A convenient one-pot synthesis of trisubstituted 1,3,5-triazines through intermediary amidinothioureas

Tetrahedron Letters

Volumn 51, Issue 11, 2010, Pages 1486-1489

  Kaila, Jitendra C ^a   Baraiya, Arshi B ^a   Pandya, Amit N ^a   Jalani, Hitesh B ^a   Sudarsanam, V ^a   Vasu, Kamala K ^a  

^a B V PATEL PHARMACEUTICAL EDUCATION AND RESEARCH DEVELOPMENT PERD CENTRE   (India)

Author keywords

1,3,5 Triazines; Amidinothioureas; Carbamidines; Thiophile

Indexed keywords

COPPER SULFATE; GUTIMINE; ISOTHIOCYANIC ACID; MERCURY CHLORIDE; SILICA GEL; TRIAZINE;

ARTICLE; CHEMICAL REACTION; DESULFURIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 75949123586     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.01.034     Document Type: Article

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20. General experimental procedure for the preparation of trisubstituted 1,3,5-triazines: To a stirred solution of isothiocyanate 1 (1 mmol) in THF (5 mL), N,N-diethylamidine 2 (1 mmol) was added at room temperature and allowed to stir for 2 h. To the stirred reaction mixture triethylamine (15 mmol) and carbamidine hydrochloride 4 (1.2 mmol) were added at room temperature. Mercury(II) chloride (1 mmol) was added slowly to the reaction mixture (slight exothermic) and the mixture was allowed to stir for another 4 h at room temperature. Initiation of the desulfurization was observed by the formation of black HgS precipitate. Progress of the reaction was monitored by TLC using ethyl acetate/hexane (3:7) as a mobile phase. After the completion of the reaction, the reaction mixture was diluted with THF (5 mL) and filtered through a Celite bed to remove the black precipitate of HgS. The filtrate was concentrated in vacuum and purified by silica gel (60-120 mesh) column chromatography using 12% ethyl acetate in hexane as a mobile phase to give triazines 5. The same experimental protocol was followed for the preparation of 2,5-diamino-1,3,5-triazines (Scheme 2, Table 1, entries 10-13) using tetramethylguanidine instead of N,N-diethylamidines.