An expedient sequential one-pot four component synthesis of novel steroidal spiro-pyrrolidine heterocycles in ionic liquid

Design, Synthesis, Anticancer Evaluation and Molecular Modeling of Novel Estrogen Derivatives

“…Arylmethylene of estrone derivatives 2a , b [33,34,35] was synthesized via Aldol condensation of estrone 1 and 2-chlorobenzaldehyde or 4-chlorobenzaldehyde in ethanol in the presence of 30% potassium hydroxide according to the previous reported procedure. Treatment of compounds 2a , b with urea or thiourea, in the presence of sodium ethoxide afforded the corresponding 2-oxopyrimidines 3a , b and 2-thioxopyrimidines 4a , b , respectively.…”

“…A mixture of 2a , b (10 mmol) [33,34,35] and urea or thiourea (12 mmol) in sodium ethoxide solution [absolute ethanol (25 mL) in the presence of sodium metal (920 mg, 40 mmol)] was refluxed for 5 hrs. The reaction mixture was evaporated under reduced pressure to dryness, and the obtained residue was solidified with water.…”

Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

“…31 Biologically important aryl-and heteroaryl-substituted functionalized spirooxindolepyrrolizidine derivatives 56 were obtained employing electrophilic alkenes 55 containing an indole unit. Apart from isatins 2 and L-proline (1), other components such as acenaphthoquinone (33) or ninhydrin (57), sarcosine (13) and alkenes 58 (bonded to a pyrrole ring) were successfully utilized. In general, the chemical yields and the diastereoselection were very high (Scheme 14).…”

“…Biologically active quinolines containing both pyrrolidine and spirooxindole core structures 86 were designed by Mohan and co-workers. The 1,3-DC was carried out using sarcosine (13) or thiazolidine-4-carboxylic acid (18) together with isatins 2, acenaphthoquinone (33), or ninhydrin (57) and with designed (E)-3-[(quinolin-3-yl)methylene]indol-2-one derivatives 85 as dipolarophiles (Scheme 24). Biological evaluation of this new spiroheterocycles 86 revealed important in vitro antioxidant, antidiabetic, and acetylcholinesterase (AChE) inhibitory activities.…”

1,3‐Dipolar Cycloadditions of Stabilized Azomethine Ylides and Electrophilic Alkenes Mediated by a Recyclable TSIL·AgOAc Catalyst

“…[19] Other examples using 1-butyl-3-methylimidazolium tetrafluoroborate, [BMIM]BF 4 , [20,21] or [BMIM]Br [22] as ionic liquids, or ionic liquid-multicomponent-MW combinations, [23,24] were described. The first [3+2] cycloaddition of azomethine ylides employing an ionic liquid medium allowed to prepare functionalized spiropyrrolidines.…”