Novel benzothiophene 1,1-dioxide deoxygenation path for the microwave-assisted synthesis of substituted benzothiophene-fused pyrrole derivatives

The reaction of C -(4-substituted-phenyl)- N -(benzoyl)- N -methylglycines with benzo[ b ]thiophene 1,1-dioxide unexpectedly gave benzothiophene-fused pyrrole derivatives in toluene under microwave irradiation via a cycloaddition and metal-free Pummerer-type sulfone deoxygenation path. In order to o...

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Bibliographic Details
Published in:Molecular diversity 2017-02, Vol.21 (1), p.53-60
Main Authors: Karakus, Hamza, Dürüst, Yasar
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Chemical synthesis
Chemistry Techniques, Synthetic
Deoxyribonucleic acid
DNA
Life Sciences
Microwave heating
Microwaves
Models, Molecular
Molecular Conformation
Organic Chemistry
Original Article
Oxygen - chemistry
Pharmacy
Polymer Sciences
Pyrroles - chemistry
Thiophenes - chemical synthesis
Thiophenes - chemistry
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Summary:The reaction of C -(4-substituted-phenyl)- N -(benzoyl)- N -methylglycines with benzo[ b ]thiophene 1,1-dioxide unexpectedly gave benzothiophene-fused pyrrole derivatives in toluene under microwave irradiation via a cycloaddition and metal-free Pummerer-type sulfone deoxygenation path. In order to obtain the desired sulfone derivatives, the sulfide group underwent oxidation with m -CPBA to afford sulfones. The structures of all the new products were elucidated by spectroscopic/physical methods and, in two cases, by X-ray diffraction. Graphical Abstract
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-016-9700-0