Synthesis of novel 8-(het)aryl-6H-pyrano[4′,3′:4,5]thieno[3,2-b]pyridines by 6-endo-dig cyclization of Sonogashira products and halolactonizations with Cu salts/NXS. Preliminary antitumor evaluation
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DOI: 10.1016/j.tet.2019.01.054
Abstract: Abstract Novel 8-(het)aryl-6H-pyrano[4′,3′:4,5]thieno[3,2-b]pyridines were prepared in good to high yields by a tandem one-pot procedure of Sonogashira coupling and 6-endo-dig lactonization from 3-bromothieno[3,2-b]pyridine-2-carboxylic acid and (het)arylalkynes. Sonogashira coupling products were also prepared from the corresponding… read more here.
Keywords: endo dig; aryl pyrano; het; novel het ... See more keywords
Catalyst and additive free 6-endo-dig cyclization of ortho-alkynylarylaldimines in water: An environmentally friendly access to isoquinolines
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DOI: 10.1016/j.tetlet.2019.151454
Abstract: Abstract A novel and sustainable route for the synthesis of isoquinoline was developed by reacting 2-ethynylbenzaldehyde with ammonium hydroxide in water. This method provides a convenient, atom-economical, and catalyst-free access to diversely substituted isoquinolines with… read more here.
Keywords: additive free; catalyst additive; water; free endo ... See more keywords
Copper-Catalyzed 6-endo-dig Cyclization-Coupling of 2-Bromoaryl Ketones and Terminal Alkynes toward Naphthyl Aryl Ethers in Water.
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DOI: 10.1021/acs.orglett.2c01654
Abstract: The cyclization-coupling reaction of 2-bromoaryl ketones and terminal alkynes is first realized by copper catalysis, which produces polyfunctional naphthyl aryl ethers in moderate to excellent yields with broad substrate scope and good functional group tolerance.… read more here.
Keywords: cyclization coupling; bromoaryl ketones; ketones terminal; endo dig ... See more keywords
A 6-endo-dig Thiolative Cyclization of Yne-Ynamides: Access to Thiodihydropyridin-2-ones.
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DOI: 10.1021/acs.orglett.2c03225
Abstract: A straightforward regioselective intramolecular 6-endo-dig cyclization of yne-tethered ynamide is herein developed. The reaction involves an intramolecular enolate attack of ketene-N,O-acetals, generated in situ from yne-ynamide and methanesulfonic acid, to the alkyne moiety activated by… read more here.
Keywords: dig thiolative; cyclization yne; access; endo dig ... See more keywords
Efficient Synthesis of 1H-Benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-one Derivatives Using Ag2CO3/TFA-Catalyzed 6-endo-dig Cyclization: Reaction Scope and Mechanistic Study
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DOI: 10.3390/molecules28052403
Abstract: A small library of 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-one derivatives was prepared in good to excellent yields, involving a Ag2CO3/TFA-catalyzed intramolecular oxacyclization of N-Boc-2-alkynylbenzimidazole substrates. In all experiments, the 6-endo-dig cyclization was exclusively achieved since the possible 5-exo-dig heterocycle… read more here.
Keywords: ag2co3 tfa; dig; benzo imidazo; endo dig ... See more keywords