Abstract
An efficient procedure to obtain the new compound 1a from ethyl acetoacetate (2a), NBS and N,N′-diethylthiourea (4a) was reported. In comparison with the traditional method to synthesize its analogues, this efficient, catalyst-free, and one-pot synthetic method is facile. The work-up procedure is easy and gives the pure target compound under milder reaction conditions in a relatively high yield of 75%.
Highlights
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The methods developed in this paper will enrich the limited arsenal for efffiiciently constructing various functionalized 2,3-dihydro-1,33--tthhiiaazzoolleess, wwhhiicchh wwoouulldd be a beneffiit for further exploration of their potent unknown biological activities
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Summary
TThhee attaetmtepmtpint ouinr resoeuarrch grersoeuaprctho acgquroiruepthettoitle accoqmupiroeundth—e3-ettihtylel- 2-ceotmhypliomuinndo—-4-3m-eetthhyyll-22-,3et-hdyihliymdirnoo-1-4,3--mtheitahzyoll-e2-,53--cdairhbyodxryol-a1t,e3-etthhiyazl oeslete-5r-(c1aar)b—oxuysliantge tehtehryelpeosrtteerd (D1aB)T—BuEsminegthtohde lreedptoorttehde DBTBE method led to the complete recovery of the starting materials. The conventional synthesis of 1a via Scheme 1 involv2edof a4 tedious work-up with very low overall yield, which could not be used efficiently. AAss ppaarrtt ooff oouurr rreecceenntt ssttuuddiieess oonn tthhee nneeww bbiioollooggiiccaall hheetteerrooccyycclliicc ccoommppoouunnddss [[1122,,1133]],, wwee nnooww rreeppoorrtt aa ssuucccceessssffuull ssiimmppllee pprroocceedduurree ttoo ssyynntthheessiizzee 11aa ffrroomm eetthhyyll aacceettooaacceettaattee ((22aa)),, NNBBSS,, aanndd NN,,NN′--ddiieetthhyylltthhiioouurreeaa ((44aa)).. WWhhiillee 11aa sshhaarreess aa ssiimmiillaarr ssttrruuccttuurree wwiitthh tthhee rreeppoorrtteedd aannaalloogguueess [[88]],, iitt wwaass ssttiillll rreeppoorrtteedd ffoorr tthhee fifirrsstt ttiimmee bbyy oouurr rreesseeaarrcchh ggrroouuppiinntthhiissppaappeerr..
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