Synthesis of heterocyclic compounds possessing the 4H-thieno[3,2-b]pyrrole moiety.
A series of novel heterocyclic combinatorial libraries containing 4H-thieno[3,2-b]pyrrole, thieno[2',3':4,5]-pyrrol[1,2-d][1,2,4]triazine and thieno[2',3':4,5]pyrrolo[1,2-a]pyrazine heterocyclic moieties were obtained by parallel solution-phase synthesis. Key steps include different reactions of initial alkyl 4H-thieno[3,2-b]-pyrrole-5-carboxylates, such as alkylation with alkylating agents; transformation of the carboxylate group into different reactive functionalities, followed by reactions with electrophilic species; intramolecular cyclizations; and amide bond formation. Simple manual techniques for parallel reactions were coupled with easy purification procedures to give high-purity final products.
Ilyin
Alexey P
AP
Chemical Diversity Research Institute, Khimki, Moscow reg. 114401, Russia.
Dmitrieva
Irina G
IG
Kustova
Veronika A
VA
Manaev
Alexandre V
AV
Ivachtchenko
Alexandre V
AV
D002853:Chromatography, Liquid; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis*; D013876:Thiophenes / Q000138:chemical synthesis*
D011758:Pyrroles; D013876:Thiophenes