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Copper‐Catalysed Cascade Synthesis of Imidazolidine–Benzothiazole and Imidazolidine–Tetrazole Hybrid Heterocycles from Bis‐thioureas by a Desulfurisation Strategy
Author(s) -
Ganesh Majji,
Sahoo Santosh K.,
Khatun Nilufa,
Patel Bhisma K.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501096
Subject(s) - benzothiazole , imidazolidine , chemistry , sodium azide , tetrazole , alkyl , azide , aryl , copper , organic chemistry , combinatorial chemistry , medicinal chemistry
The in situ generated bis‐thioureas obtained by treating aryl/alkyl isothiocyanates with aliphatic 1,2‐diamines, upon treatment with Cu I or Cu II salts, depending on their quantity and the reaction conditions, furnished either imidazolidinecarbothioamide (ImCAT) or imidazolidine–benzothiazole (ImBT) hybrid molecules. The same reactions in the presence of sodium azide yielded imidazolidine–tetrazoles (ImTets). The products were obtained in good yields at room temperature with all these processes taking place in a single pot. This is a perfect illustration of Cu salts serving as both desulfurising as well as C–H activating agents at ambient temperature.