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Paper | Regular issue | Vol 78, No. 7, 2009, pp.1729-1759
Published online, 19th March, 2009
DOI: 10.3987/COM-09-11668
New Thiazolidinone and Triazinethione Conjugates Derived from Amino-β-lactams

Katarina Radolović, Ivan Habuš,* and Bogdan Kralj

*Ruđer Bošković Institute, Bijenička c. 54, P.O.B. 180, HR-10002 Zagreb, Croatia


Thioureas 3a-s, generated from amino-β-lactams 1a-c, were used to achieve two different cyclizations: (i) condensation with ethyl bromoacetate which resulted in the formation of a variety of iminothiazolidinones 4a/a'-n, and (ii) condensation with aqueous formaldehyde and methylamine which resulted in the formation of triazinethiones 5a-g. The condensation of thioureas 3b-f, 3h and 3m-s (R1 = cyclohexyl, exo-norbornyl, aryl, R2 = β-lactam) with ethyl bromoacetate proceeded with high regioselectivity leading exclusively to the formation of a single regioisomer A of iminothiazolidinones 4b-n. However, the cyclization of thiourea 3a (R1 = n-hexyl, R2= β-lactam) with ethyl bromoacetate led to the formation of a mixture of two regioisomers A (minor) and B (major) of the iminothiazolidinones 4a/a' in the ratio 23:77. Furthermore, condensation of thioureas 3d, 3g, 3i-l and 3n with aqueous formaldehyde and methylamine, furnished triazinethiones 5a-g.