Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles

Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles

One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75–94%) was achieved within 60mi...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 54; no. 21; pp. 2693 - 2695
Main Authors: Bommegowda, Yadaganahalli K., Lingaraju, Gejjalagere S., Thamas, Saji, Vinay Kumar, Koravangala S., Pradeepa Kumara, Challanayakanahally S., Rangappa, Kanchugarakoppal S., Sadashiva, Marilinganadoddi P.
Format: Journal Article
Language:English
Published: Elsevier Ltd 22-05-2013
Subjects:
Amides
Benzimidazoles
Benzothiazoles
Boron
Boron trifluoride etherate
Condensing
Functional groups
Halogens
o-Aminothiophenol
o-Diaminoarene
Solvents
Synthesis (chemistry)
Tetrahedrons
Weinreb amide
Benzimidazoles
Weinreb amide
Boron trifluoride etherate
o-Diaminoarene
Benzothiazoles
o-Aminothiophenol
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Summary:One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75–94%) was achieved within 60min. Weinreb amide shows high selectivity in the reaction, even in presence of other active functional groups such as carboxyl, halogen, cyano, and methoxy. [Display omitted]
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.03.075