ABSTRACT
Correction for 'A metal-free cascade reaction of ß-halo-α,ß-unsaturated aldehydes and 1,4-dithiane-2,5-diols: synthesis of polycyclic 2-formylthiophenes' by Limi Goswami et al., Org. Biomol. Chem., 2017, 15, 6470-6473.
ABSTRACT
A metal-free cascade reaction strategy has been developed for the synthesis of novel polycyclic 2-formylthiophenes from ß-halo-α,ß-unsaturated aldehydes and 1,4-dithiane-2,5-diols. A recyclable polymer supported organic base was used to perform the reaction process. This synthetic protocol was applied to synthesize several novel polycyclic thiophenes including steroidal D-ring annelated thiophene. Our synthetic strategy provides a high yield of thiophenes, avoids a tedious work-up procedure and minimizes the formation of waste.
ABSTRACT
A three-component cascade method has been developed for the direct synthesis of polysubstituted pyridines. This strategy provides a very convenient route to pyridines using a variety of ß-bromo-α,ß-unsaturated aldehydes, 1,3-diketones, and ammonium acetate without any additional catalyst or metal salt under mild conditions. A variety of ß-ketoesters and 4-hydroxycoumarin were also used instead of 1,3-diketones for the diverse synthesis of polycyclic pyridines. One of the synthesized pyridines has been unambiguously established by a single crystal XRD study. All of the synthesized pyridine derivatives were evaluated for their antiproliferative properties in vitro against the human cancer cell lines HeLa, Me180, and ZR751. Compounds 4{4,1} and 4{2,4} showed significant cytotoxicity in the human breast cancer cell line ZR751 and cervical cancer cell line Me180, respectively, and a few other compounds were found to have moderate activities.
Subject(s)
Antineoplastic Agents/chemical synthesis , Pyridines/chemical synthesis , Antineoplastic Agents/pharmacology , Breast Neoplasms/drug therapy , Breast Neoplasms/pathology , Cell Line, Tumor , Cell Survival/drug effects , Cytotoxins/chemistry , Cytotoxins/pharmacology , Female , Humans , Polycyclic Compounds/chemical synthesis , Polycyclic Compounds/pharmacology , Pyridines/pharmacology , Uterine Cervical Neoplasms/drug therapy , Uterine Cervical Neoplasms/pathologyABSTRACT
A novel heterogeneous catalytic hydrogenation-hydrogenolysis strategy has been developed for the α-methylation of ketones via enaminones using DMF dimethyl acetal as carbon source. This strategy provides a very convenient route to α-methylated ketones using a variety of ketones without any base or oxidant.