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1.
J Org Chem ; 86(9): 6755-6764, 2021 May 07.
Artículo en Inglés | MEDLINE | ID: mdl-33847128

RESUMEN

An atom economic procedure for the regioselective synthesis of bridged seven-membered-ring compounds from simple reactants such as ynones and indene-1,3-dione has been developed. This process was realized through the one-pot reactions of ring-expansion of indene-1,3-dione with alkynyl ketones and successive formal [4+2] cycloaddition. The Michael addition reaction is the key for the regioselectivity of the formal [4+2] cycloaddition.

2.
Org Biomol Chem ; 15(12): 2497-2500, 2017 Mar 22.
Artículo en Inglés | MEDLINE | ID: mdl-28266674

RESUMEN

Transition-metal free insertions of alkynes into carbon-carbon σ-bonds of ethanones have been reported. These tandem reactions offer an efficient synthesis of hydroxydienones and multi-substituted chromones. This is the first example of base-promoted insertion reactions of isolated carbon-carbon triple bonds into carbon-carbon σ-bonds with active methylene compounds bearing only one electron-withdrawing group.

3.
Chemistry ; 22(50): 17936-17939, 2016 Dec 12.
Artículo en Inglés | MEDLINE | ID: mdl-27735095

RESUMEN

The transition-metal-free insertion of isolated alkynes into carbon-carbon σ-bonds of unstrained cyclic ß-dicarbonyl compounds has been reported. These tandem reactions offer an efficient synthesis of medium-sized ring or fused-ring compounds through ring expansion. The methodology has the potential to be widely used throughout organic synthesis due to the easily accessible starting materials and mild reaction conditions.

4.
Org Biomol Chem ; 14(7): 2177-81, 2016 Feb 21.
Artículo en Inglés | MEDLINE | ID: mdl-26788797

RESUMEN

An efficient tandem Au(i)/TsOH-catalyzed reaction of enaminones with diazo compounds for the synthesis of pyrroloquinolinone derivatives under mild reaction conditions has been developed. This methodology was realized by relay actions of Au and TsOH in a one-pot multistep manner. Initially, the Au-catalyzed reaction of enaminones with diazo compounds affords chemo- and diastereoselective C(sp(2))-H functionalized products, which then undergo subsequent intramolecular cyclization/rearrangement to give pyrroloquinolinone derivatives under the catalysis of TsOH.

5.
Org Lett ; 20(7): 1744-1747, 2018 04 06.
Artículo en Inglés | MEDLINE | ID: mdl-29533628

RESUMEN

A novel ring expansion reaction of indene-1,3-dione with alkynyl ketones under transition-metal-free conditions has been developed. This process offers an efficient and direct way to synthesize benzoannulated seven-membered rings or fused-ring compounds through C-C σ-bond activation. Notable features of the procedure include easily accessible starting materials, good functional group tolerance, and high atom economy.

6.
Chem Commun (Camb) ; 54(78): 11009-11012, 2018 Sep 27.
Artículo en Inglés | MEDLINE | ID: mdl-30215063

RESUMEN

An efficient and atom-economical methodology for the synthesis of multi-substituted carbazoles starting from α-aryl ketones and ynones under mild reaction conditions has been developed. This process goes through Cs2CO3 promoted C-C σ-bond activation of α-aryl ketones followed by highly selective C-H bond activations and C-C bond fragmentations in a one-pot operation.

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