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New Thiazolidinone and Triazinethione Conjugates Derived from Amino-beta-lactams


Radolović, Katarina; Habuš, Ivan; Kralj, Bogdan
New Thiazolidinone and Triazinethione Conjugates Derived from Amino-beta-lactams // Heterocycles, 78 (2009), 7; 1729-1759 doi:10.3987/COM-09-11668 (međunarodna recenzija, članak, znanstveni)


Naslov
New Thiazolidinone and Triazinethione Conjugates Derived from Amino-beta-lactams

Autori
Radolović, Katarina ; Habuš, Ivan ; Kralj, Bogdan

Izvornik
Heterocycles (0385-5414) 78 (2009), 7; 1729-1759

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
B-Lactam ; Isothiocyanate ; Thiourea ; Iminothiazolidinone ; Triazinethione

Sažetak
Thioureas 3a-s, generated from amino-b-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 = b-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 thiurea 3a (R1 = n-hexyl, R2 = b-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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982915-2948 - Amino-beta-laktami - intermedijari u sintezi biološki interesantnih spojeva (Vlasta Tomašić, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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