Synthesis of spiro[imidazole-2,2′-pyrroles] by reaction of 4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with urea

Amination of 5-Spiro-Substituted 3-Hydroxy-1,5-dihydro-2H-pyrrol-2-ones

“…This reaction proceeded smoothly and yielded target compounds 1a–g in excellent yields (isolated yields of 86–98%). The spectral data of compounds 1a–g were in good agreement with other similar spiro HDPs reported by our group earlier [ 18 , 19 ]. Compounds 1a–g were isolated by simple filtration from the reaction mixture and were sufficiently pure to be used in further experiments without additional purification.…”

“…Initially, we prepared HDPs bearing a rigid spiro substituent at the C 5 position, compounds 1a–g , by the reaction of compounds 2a–g with dicyclohexylurea ( Scheme 3 ) [ 17 , 18 , 19 ]. This reaction proceeded smoothly and yielded target compounds 1a–g in excellent yields (isolated yields of 86–98%).…”

N-tert-Butyl-2-{2-[2-(4-chlorophenyl)-4-hydroxy-1-(5-methylisoxazol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N-(4-methoxyphenyl)acetamido}-2-(4-methoxyphenyl)acetamide methanol monosolvate: single-crystal X-ray diffraction study and Hirshfeld surface analysis

“…A search of the Cambridge Structural Database (CSD Version 5.42, update of November 2020; Groom et al, 2016) for the 3hydroxy-1,5-dihydro-pyrrol-2-one fragment revealed 79 hits. Only 27 of these hits contain a fragment with the same structure as that of the title compound [refcodes: BOQXEN (del Corte et al, 2019), CIKPAQ (Sarkar et al, 2018), EVIYUD (Aliev et al, 2003b), GEJZAY (Mashevskaya et al, 2011), GIMGEQ (Sarkar et al, 2013), GITCAQ, GITDEV (Saha et al, 2017), IRUBUS (Aliev et al, 2003a), LIFBEJ, LIFBOT (Sun et al, 2011), NUXPIG (Wiedemann et al, 2009), PADHUA (Zonouz et al, 2015), PASTOT (Nicolaou et al, 2005), QIPNAH (Bhajammanavar et al, 2019), ROHNAG (Hosseinzadeh et al, 2019), TOMPER (Sakhno et al, 2008), UJEXOY (Ahankar et al, 2016), VILQEP (Gein et al, 2018), VIPNAJ (Mylari et al, 1991), VIQDOP (Guseinov et al, 2006), VOWGAP (Kazakov et al, 1990), WAPMIM (Dubovtsev et al, 2016), XINHIL (Aliev et al, 2001), XOKRAT, XOKRAT01 (Ramazani et al, 2019), YAJMOM (Wei et al, 2004), YIYFAP (Denislamova et al, 2014)]. All these structures and the title compound have the same electron density distribution within the 3-hydroxy-1,5-dihydropyrrol-2-one fragment.…”