Catalyst-Free α-Allylation of Dihydroisoquinolines with Morita–Baylis–Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines DOI
Siyu Wang, Yuhan Li,

Zhuoqi Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3636 - 3649

Published: March 2, 2023

In this work, a mild and efficient catalyst-free α-allylation of 3,4-dihydroisoquinoline imines with Morita-Baylis-Hillman (MBH) carbonates was reported. The scopes 3,4-dihydroisoquinolines MBH as well gram-scale synthesis were investigated, densely functionalized adducts obtained in moderate to good yields. synthetic utility these versatile synthons further demonstrated by the facile diverse benzo[a]quinolizidine skeletons.

Language: Английский

Organocatalytic Enantioselective Synthesis of Polycyclic Benzosultams from 2-Amino-β-nitrostyrenes with Cyclic N-Sulfonyl Ketimines DOI
Yoseop Kim, Ji Won Han, Sung‐Gon Kim

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1472 - 1477

Published: Feb. 13, 2024

A highly efficient enantioselective [4 + 2] cycloaddition of 2-amino-β-nitrostyrenes with cyclic N-sulfonyl ketimines has been developed. This reaction utilizes an organocatalytic approach, employing a multiple-hydrogen-bonding bifunctional squaramide-based catalyst. The process allows for the precise synthesis chiral polycyclic benzosultams, showcasing intricate structures that incorporate quaternary centers. Noteworthy outcomes this method include high yields excellent enantioselectivities and diastereoselectivities (up to 97% yield, 96% ee, >20:1 dr).

Language: Английский

Citations

4
Palladium‐Catalyzed [4+2] and [6+2] Dipolar Cycloadditions for the Construction of Benzo[d]isothiazole 1,1‐Dioxide Fused 1,3‐Oxazinanes and 1,3‐Oxazocanes† DOI Open Access
Lei Chen,

Hongling Xie,

Yu Xue

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(8), P. 829 - 834

Published: Dec. 8, 2023

Comprehensive Summary The Pd‐catalyzed dipolar cycloaddition represents a significant synthetic strategy for the construction of useful heterocyclic compounds. This study developed [4+2] and [6+2] reactions benzo[ d ]isothiazole 1,1‐dioxides (BDs) leading to synthesis BD‐fused 1,3‐oxazinane 1,3‐oxazocane derivatives, respectively. In particular, 1,3‐oxazinanes demonstrated regio‐ enantioselective characteristics, resulting in products with good yields, enantioselectivity regioselectivity (if applicable). Furthermore, reaction this work represented first medium‐sized ring compounds based on BDs.

Language: Английский

Citations

9
Organocatalytic Asymmetric Michael Reactions of Cyclic N-Sulfonylimines with Nitroalkenes or 2-Nitroallylic Acetates DOI
Yurim Kim,

Yeongju Kim,

Sung‐Gon Kim

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 25, 2025

A highly efficient enantioselective Michael addition of cyclic N-sulfonylimines with nitroalkenes has been developed, utilizing a bifunctional squaramide catalyst. This approach achieves remarkable results, delivering products high yields and outstanding stereoselectivities, reaching up to 97% yield, >20:1 dr, >99% ee. Furthermore, an asymmetric tandem reaction 2-nitroallylic acetates established. innovative methodology involves Michael/intramolecular aza-Michael cascade, leading the formation enantioenriched benzosultam-fused tricyclic compounds excellent stereoselectivities (up dr ee).

Language: Английский

Citations

0
Rhodium-catalyzed addition reactions of benzylic C–H bonds to cyclic N-sulfonyl ketimines via π-coordination DOI
Yuntong Li,

Hang Shi

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(3), P. 108650 - 108650

Published: June 7, 2023

Language: Английский

Citations

6
One-pot π-extension approach of iminoindoles-to-α-carbolines as blue-light emitters using the cooperative basic system DOI

Rajni Lodhi,

S Banuprakash Goud,

Sampak Samanta

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(32), P. 14163 - 14169

Published: Jan. 1, 2024

Efficient access to α-carbolines was achieved via a domino reaction between iminoindoles and arylidene malononitriles using DABCO/NaHCO 3 as cooperative basic system. The synthesized scaffolds display blue emissions with good quantum yields.

Language: Английский

Citations

2
CeCl3-Catalyzed C–H Alkylation of N-Sulfonyl Ketimines with Alkanes and Ether via Photoinduced Ligand-to-Metal Charge Transfer DOI
Bin Zhou, Min Dong, Wei Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(24), P. 18337 - 18343

Published: Dec. 9, 2024

A cerium-catalyzed C–H alkylation of N-sulfonyl ketimines with low-cost and readily available alkanes as alkyl sources was developed. This transformation proceeded through the synergy photoinitiated ligand-to-metal charge transfer (LMCT) using a chlorine radical an HAT reagent air green oxidant. series alkylated were synthesized moderate to good yields in highly atom-economic manner under chemical oxidant-free conditions.

Language: Английский

Citations

2
Photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines DOI Creative Commons
Jingjing Wang, Feng Li, Kai Liu

et al.

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 1, 2023

We first describe a photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines. The desired products were generated in moderate to good yields with wide substrate scope under mild reaction conditions. mechanistic study revealed radical process. In addition, the usefulness organic synthesis was proved by scale-up as well late-stage modification drug-like molecules.

Language: Английский

Citations

5
Cu(OAc)2/DABCO-mediated domino reaction of vinyl malononitriles with cyclic sulfamidate imines: access to 6-hydroxyaryl-2-aminonicotinonitriles DOI

S Banuprakash Goud,

Soumitra Guin,

Meher Prakash

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 20(2), P. 352 - 357

Published: Dec. 11, 2021

An efficient DABCO/Cu(OAc) 2 promoted one-pot access to pharmacologically exciting highly substituted 6-hydroxyaryl-2-aminonicotinonitriles in good high yields is reported.

Language: Английский

Citations

10
Regioselective access to di- and trisubstituted pyridines via a metal-oxidant-solvent-free domino reaction involving 3-chloropropiophenones DOI
Ashvani K. Patel,

Shikha Singh Rathor,

Sampak Samanta

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(34), P. 6759 - 6765

Published: Jan. 1, 2022

A remarkable metal-oxidant-solvent- and base-free domino route for regioselective access to a wide range of 2,4-di- 2,3,4/6-trisubstituted pyridines including carbo- heterocyclic fused is reported. This [3C + 2C 1N] cyclization reaction occurs between 3-chloropropiophenones (3C units), enolizable acyclic/cyclic ketones (2C sources) NH4OAc as robust N source under neat conditions an open atmosphere, producing new C=C C=N-C bonds in highly chemo- manners. Interestingly, this eco-friendly method has many positive features: excellent functional group tolerance, broad substrate scope, good regioselectivities, promising yields, no-unwanted products, neutral appropriateness large-scale synthesis. Mechanism studies reveal that the situ generated β-amino ketone from 3-chloropropiophenone ammonium salt undergoes C=N bond formation with followed by intramolecular process (C=C bond), which are decisive steps pyridine

Language: Английский

Citations

7
AgOTf/Et3N Cooperative Catalysis Enabled One‐Pot Access to α‐(Indolizinylethyl)‐Substituted N‐Sulfonyl Ketimines via an Imino‐Alkyne Cyclization DOI

Rajni Lodhi,

Ashvani K. Patel, Sampak Samanta

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(12)

Published: Nov. 1, 2022

Abstract The β‐Csp 3 −H functionalization of N‐sulfonyl ketimines with 2‐(2‐enynl)pyridines/quinolines via a cooperative Ag(I)‐/organobase‐catalyzed 5‐ endo‐dig cyclization‐addition reaction is reported. This successive C−N/C−C bond‐making provides simple and atom‐economical technique for granting diverse set 1,3‐disubstituted indolizines/pyrrolo[1,2‐ ]quinolines possessing synthetically resourceful ketimine moiety. Moreover, our designed strategy applies to broad substrates allows various functionalities. Furthermore, this has many imperative synthetic points such as mild conditions, low catalyst loading, acceptable chemical yields highly diastereoselective (up ≤93 : 7 dr). moiety indolizine was easily transmuted into the reputed classes coumarin benzofuran derivatives.

Language: Английский

Citations

7