Cascade of the acylation/intramolecular oxo-Diels–Alder reaction for the diastereoselective synthesis of thienyl substituted hexahydropyrano[3,4-c]pyrrole-1,6-diones

Zaytsev, Vladimir P.; Surina, Nataliya S.; Pokazeev, Kuzma M.; Shelukho, Evgeniya R.; Yakovleva, Elizaveta D.; Nadirova, Maryana A.; Новиков, Роман А.; Хрусталев, В. Н.; Зубков, Федор И.

doi:10.1016/j.tetlet.2023.154434

Cited by 3 publications

(2 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We also found the conditions for the reaction of benzothienylallylamine 7t 11 bearing a methyl group at the third position of the thiophene ring with maleic anhydride. It was previously shown 11 that this type of reaction in boiling toluene stops at the stage of maleinamide 14t formation. More severe conditions led to undesirable decomposition of the mixture.…”

Section: Resultsmentioning

confidence: 92%

Application of the intramolecular Diels–Alder vinylarene (IMDAV) reaction for the synthesis of benzo-, carbocyclo-, thienothiopheneisoindolecarboxylic acids and its limitations

Yakovleva,

Shelukho,

Nadirova

et al. 2024

Org. Biomol. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 92%

Application of the intramolecular Diels–Alder vinylarene (IMDAV) reaction for the synthesis of benzo-, carbocyclo-, thienothiopheneisoindolecarboxylic acids and its limitations

Yakovleva,

Shelukho,

Nadirova

et al. 2024

Org. Biomol. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Despite the large number of examples of the synthesis of dipyrromethanes, there is a lack of literature data on the synthesis of thiophene-substituted dipyrromethanes. Therefore, we used 3-benzylthiophenecarboxaldehyde (Zaytsev et al, 2023), which, when reacted with pyrrole, gives the target dipyrromethane 1 in 70% yield (Fig. 1).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 3-benzyl-2-[bis(1H-pyrrol-2-yl)methyl]thiophene

Sadikhova,

Atioğlu,

Guliyeva

et al. 2024

Acta Cryst E

Self Cite

View full text Add to dashboard Cite

In the title compound, C20H18N2S, the asymmetric unit comprises two similar molecules (A and B). In molecule A, the central thiophene ring makes dihedral angles of 89.96 (12) and 57.39 (13)° with the 1H-pyrrole rings, which are bent at 83.22 (14)° relative to each other, and makes an angle of 85.98 (11)° with the phenyl ring. In molecule B, the corresponding dihedral angles are 89.49 (13), 54.64 (12)°, 83.62 (14)° and 85.67 (11)°, respectively. In the crystal, molecular pairs are bonded to each other by N—H...N interactions. N—H...π and C—H...π interactions further connect the molecules, forming a three-dimensional network. A Hirshfeld surface analysis indicates that H...H (57.1% for molecule A; 57.3% for molecule B), C...H/H...C (30.7% for molecules A and B) and S...H/H...S (6.2% for molecule A; 6.4% for molecule B) interactions are the most important contributors to the crystal packing.

show abstract

Six-membered ring systems: With O and/or S atoms

Santos,

Silva

2024

Progress in Heterocyclic Chemistry

View full text Add to dashboard Cite

Cascade of the acylation/intramolecular oxo-Diels–Alder reaction for the diastereoselective synthesis of thienyl substituted hexahydropyrano[3,4-c]pyrrole-1,6-diones

Cited by 3 publications

References 38 publications

Application of the intramolecular Diels–Alder vinylarene (IMDAV) reaction for the synthesis of benzo-, carbocyclo-, thienothiopheneisoindolecarboxylic acids and its limitations

Application of the intramolecular Diels–Alder vinylarene (IMDAV) reaction for the synthesis of benzo-, carbocyclo-, thienothiopheneisoindolecarboxylic acids and its limitations

Crystal structure and Hirshfeld surface analysis of 3-benzyl-2-[bis(1H-pyrrol-2-yl)methyl]thiophene

Six-membered ring systems: With O and/or S atoms

Contact Info

Product

Resources

About