Metal- and Solvent-Free Approach to Diversely Substituted Picolinates via Domino Reaction of Cyclic Sulfamidate Imines with β,γ-Unsaturated α‑Ketocarbonyls

An efficient, solvent-free, and eco-friendly domino reaction of 5/6-membered cyclic sulfamidate imines with a variety of β,γ-unsaturated α-ketocarbonyls in neat conditions under MW irradiation promoted by DABCO as a solid organobase has been developed for the rapid construction of a novel class of densely functionalized picolinates. This interesting metal–solvent-free tactic allows a wide range of useful functionalities on the aryl rings and delivers good to excellent yields of the aforesaid aza-heterocycles within short time spans (20–40 min). A biologically promising imidazo­[1,2-<i>a</i>]­pyridine was successfully synthesized through our unique procedure

Access to 4,6-Diarylpicolinates via a Domino Reaction of Cyclic Sulfamidate Imines with Morita–Baylis–Hillman Acetates of Nitroolefins/Nitrodienes

An interesting domino reaction of 5-membered cyclic sulfamidate imines with a variety of Morita–Baylis–Hillman acetates of nitroolefins/nitrodienes in the presence of DABCO as an organic base at 55 °C is reported for the first time. This new synthetic strategy provides a series of pharmacologically interesting 4,6-diarylpicolinates in high to excellent yields and allows several compatible functionalities on aryl rings. Moreover, the biologically interesting imidazo­[1,2-<i>a</i>]­pyridine (alpidem derivative) has been prepared in high chemical yield through a unique procedure

Access to 4,6-Diarylpicolinates via a Domino Reaction of Cyclic Sulfamidate Imines with Morita–Baylis–Hillman Acetates of Nitroolefins/Nitrodienes

An interesting domino reaction of 5-membered cyclic sulfamidate imines with a variety of Morita–Baylis–Hillman acetates of nitroolefins/nitrodienes in the presence of DABCO as an organic base at 55 °C is reported for the first time. This new synthetic strategy provides a series of pharmacologically interesting 4,6-diarylpicolinates in high to excellent yields and allows several compatible functionalities on aryl rings. Moreover, the biologically interesting imidazo­[1,2-<i>a</i>]­pyridine (alpidem derivative) has been prepared in high chemical yield through a unique procedure

Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and Spirooxindoles via Allylic Alkylation of Morita–Baylis–Hillman Carbonates of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO

An efficient, organocatalytic, and ecofriendly method has been developed for the quick construction of a wide array of 3,3-disubstituted oxindoles in good to excellent yields and diastereomeric ratio (up to ≤96:4) with excellent functional group tolerance via an allylic alkylation reaction of cyclic sulfamidate imines with a number of MBH carbonates of isatins in 2-MeTHF as an environmentally benign solvent at room temperature using 5 mol % of DABCO. Furthermore, a metal-free-based one-shot synthesis of a medicinally promising polycyclic spirooxindole with an all-carbon spirocenter has been achieved with outstanding dr value (up to ≤99:1)

Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and Spirooxindoles via Allylic Alkylation of Morita–Baylis–Hillman Carbonates of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO

An efficient, organocatalytic, and ecofriendly method has been developed for the quick construction of a wide array of 3,3-disubstituted oxindoles in good to excellent yields and diastereomeric ratio (up to ≤96:4) with excellent functional group tolerance via an allylic alkylation reaction of cyclic sulfamidate imines with a number of MBH carbonates of isatins in 2-MeTHF as an environmentally benign solvent at room temperature using 5 mol % of DABCO. Furthermore, a metal-free-based one-shot synthesis of a medicinally promising polycyclic spirooxindole with an all-carbon spirocenter has been achieved with outstanding dr value (up to ≤99:1)

Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and Spirooxindoles via Allylic Alkylation of Morita–Baylis–Hillman Carbonates of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO

An efficient, organocatalytic, and ecofriendly method has been developed for the quick construction of a wide array of 3,3-disubstituted oxindoles in good to excellent yields and diastereomeric ratio (up to ≤96:4) with excellent functional group tolerance via an allylic alkylation reaction of cyclic sulfamidate imines with a number of MBH carbonates of isatins in 2-MeTHF as an environmentally benign solvent at room temperature using 5 mol % of DABCO. Furthermore, a metal-free-based one-shot synthesis of a medicinally promising polycyclic spirooxindole with an all-carbon spirocenter has been achieved with outstanding dr value (up to ≤99:1)

Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and Spirooxindoles via Allylic Alkylation of Morita–Baylis–Hillman Carbonates of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO

An efficient, organocatalytic, and ecofriendly method has been developed for the quick construction of a wide array of 3,3-disubstituted oxindoles in good to excellent yields and diastereomeric ratio (up to ≤96:4) with excellent functional group tolerance via an allylic alkylation reaction of cyclic sulfamidate imines with a number of MBH carbonates of isatins in 2-MeTHF as an environmentally benign solvent at room temperature using 5 mol % of DABCO. Furthermore, a metal-free-based one-shot synthesis of a medicinally promising polycyclic spirooxindole with an all-carbon spirocenter has been achieved with outstanding dr value (up to ≤99:1)

Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and Spirooxindoles via Allylic Alkylation of Morita–Baylis–Hillman Carbonates of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO

An efficient, organocatalytic, and ecofriendly method has been developed for the quick construction of a wide array of 3,3-disubstituted oxindoles in good to excellent yields and diastereomeric ratio (up to ≤96:4) with excellent functional group tolerance via an allylic alkylation reaction of cyclic sulfamidate imines with a number of MBH carbonates of isatins in 2-MeTHF as an environmentally benign solvent at room temperature using 5 mol % of DABCO. Furthermore, a metal-free-based one-shot synthesis of a medicinally promising polycyclic spirooxindole with an all-carbon spirocenter has been achieved with outstanding dr value (up to ≤99:1)