The ongoing study is a Ugi-azide four-component reaction for the synthesis of 1,5-disubstituted tetrazole(1,5-DST), which involves an aldehyde, different amines, isocyanides, and as azide’s source the Trimethylsilylazide (TMSN3), in water as solvent using as catalyst the tetradecyltrimethylammonium bromide (TTAB) with a load of (10% mole), which provides a hydrophobic micellar reaction site. This approach is a step toward a green chemistry reaction of 1,5 disubstituted tetrazole. A serie of 1, 5- disubstituted tetrazole was synthesized by engaging a large substrate scope, leading to yields between 43% and 56%, which are compared afterwards with those obtained with methanol as solvent. The results were confirmed by HRMS, IR, and 1D NMR experiments.
Abstract:We have previously reported a new synthesis of amides from esters and amines under microwave irradiation, offering much higher yields than those achieved with conventional heating [1]. We have now extended these studies to the ring closure of neat iminoesters I2, I3 and I4-I6 to give five-and six-membered ring lactams L5, L6 and larger lactams L7-L9 (where I means imine and L means lactam), respectively, under both classical heating conditions and microwave irradiation.
 We here report an efficient microwave-assisted protocol for the synthesis of new arylimino-thiazolylidene-2-thiazolidin-4-ones 6 and their azarhodacyanines derivatives 7 with quantitative yield from 2'-(methylthio)-4'-oxo-3H,4'H-[2,5-bithiazolylidene]-3'-ium tosylates 5 and 2-arylimino-5-(thiazol-2(3H)-ylidene) thiazolidin-4-ones 6, respectively, using as starting material the 4-thiazoline-2-thiones 1 and 3-methyl-2-thioxo-1,3-thiazolidin-4-one 3. The transformation of the tosylate salts 5 into their arylimino derivatives 6 has not been reported to date.
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