Spirobarbiturates with a pyrrolizidine moiety: synthesis, structure and biological evaluation

• Arthur A. Puzyrkov,
• Andrew S. Drachuk,
• Ekaterina A. Popova,
• Alexander V. Stepakov and
• Vitali M. Boitsov

Beilstein J. Org. Chem. 2026, 22, 274–288, doi:10.3762/bjoc.22.20

• 10.3762/bjoc.22.20 Abstract Polycyclic spirobarbiturates containing a pyrrolizidine moiety were synthesized via a one-pot three-component 1,3-dipolar cycloaddition reaction of alloxan, ʟ-proline and N-substituted maleimides. The reaction stereoselectivity was found to depend on the nature of substituents

• ; pyrrolizidine moiety; spirobarbiturates; three-component reactions; Introduction The history of barbiturates dates back to 1863, when the young Adolf von Baeyer first synthesized barbituric acid [1][2]. In 1903, the drug marketed under the trade name barbital (veronal©) became commercially available as a

• 21st century, this research culminated in the approval of the first drug whose active molecule contained a spirobarbiturate scaffold – zoliflodacin© (Scheme 1) [7]. Due to the significance of spirobarbiturates, numerous approaches have been devised for their synthesis [13][14][15][16][17][18][19

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

• Jiang-Song Zhai and
• Da-Ming Du

Beilstein J. Org. Chem. 2022, 18, 25–36, doi:10.3762/bjoc.18.3

• through a gram-scale synthesis, one-pot three-component reactions and further transformation experiments of the products. Keywords: asymmetric catalysis; cyclization reaction; Michael addition; one-pot three-component reaction; spirobarbiturates; Introduction Indane scaffolds exist in various

• cascade reagent with the indane framework, namely, 2-isothiocyanato-1-indanone (Scheme 1a) [15], but research on its participation in the construction of chiral compounds has been relatively low [16][17]. On the other hand, as a kind of vital spiroheterocyclic derivatives, spirobarbiturates show a wide

• or new methodologies to construct the spirobarbiturates with diverse structures. In recent years, good progress has been achieved in the construction of racemates of spirobarbiturates and the enantioselective synthesis [24][25][26][27][28][29], but only limited progress has been made in the