Copper‐Catalyzed Ring‐Opening (3+2) Annulation of Cyclopropenones with Ketoxime Acetates: Access to 1,2‐Dihydro‐pyrrol‐3‐ones Bearing a Quaternary Carbon Center DOI
Zhen‐Hua Wang, Ping Yang, Yanping Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(18)

Published: April 15, 2022

Abstract A Cu(I)‐catalyzed ring‐opening (3+2) annulation of cyclopropenones with ketoxime acetates has been developed. In disclosed protocol, are selected as C−N splicing unit to participate in the transformation process, furnishing a sequence highly functional 1,2‐dihydro‐pyrrol‐3‐one derivatives good isolated yields. Besides, scale‐up reaction is conducted demonstrate practicability developed methodology and tentative mechanism for also proposed.

Language: Английский

One-Pot Synthesis of 3-Methyl-2-arylimidazo[1,2-a]pyridines Using Calcium Carbide as an Alkyne Source DOI
Wei Chen, Zheng Li

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 87(1), P. 76 - 84

Published: Dec. 22, 2021

An efficient method for the construction of 3-methyl-2-arylimidazo[1,2-a]pyridines from reactions calcium carbide, 2-aminopyridines, and aromatic aldehydes is described. The notable advantages this strategy include use an inexpensive concise solid alkyne source, cheap readily available raw materials, wide-scope substrates, a simple work-up procedure.

Language: Английский

Citations

37
Sodium Alginate: An Efficient Biopolymeric Catalyst for Green Synthesis of Phenylimidazo[1,2-a]Pyridine Derivatives DOI

Shiva Zafari,

Ramin Ghorbani‐Vaghei,

Sedigheh Alavinia

et al.

Polycyclic aromatic compounds, Journal Year: 2022, Volume and Issue: 43(2), P. 1042 - 1055

Published: Jan. 4, 2022

Herein, we report the synthesis of phenyl imidazo[1,2-a]pyridine derivatives at mild conditions using sodium alginate as a green bio-organocatalyst and TBBDA (N, N, N′, N′-tetrabromobenzene-1,3-disulfonamide) brominating agent. The desired products were obtained in high to excellent yields with purities shorter reaction time under conditions.

Language: Английский

Citations

11
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
High-performance NiFe2O4 spinel catalysts: Recyclability and efficiency in multicomponent reactions DOI
Henrique P. Mota, João M. Anghinoni, Emilly C. Silva

et al.

Journal of Organometallic Chemistry, Journal Year: 2024, Volume and Issue: 1025, P. 123478 - 123478

Published: Dec. 14, 2024

Language: Английский

Citations

1
Synthesis and reactivity of 3-(1-alkynyl)chromones DOI
Vyacheslav Ya. Sosnovskikh

Russian Chemical Reviews, Journal Year: 2020, Volume and Issue: 90(4), P. 511 - 527

Published: Oct. 27, 2020

For the first time, literature data on methods of synthesis and reactivity 3-(1-alkynyl)chromones are summarized systematized. The main method for obtaining these compounds is Sonogashira cross-coupling reaction 3-halochromones with terminal acetylenes, their most important chemical properties include transformation into furans, reactions dinucleophiles, ambiphilic [4+2]- [4+3]-cyclizations, also dimerization mixed condensation 2-methyl-3-(1-alkynyl)chromones due to vinylogous methyl group. Except oxacyclization transformations accompanied by pyrone ring transformation, in which not only carbonyl group but triple bond can participate. This significantly increases synthetic value ensures production more complex heterocyclic systems based them. mechanisms discussed, conditions implementation yields resulting products indicated. bibliography includes 80 references.

Language: Английский

Citations

7
Ag(I)‐Promoted Decarboxylative Annulation of Alkynoic Acids towards 2‐Arylimidazo[1,2‐a]pyridines DOI
Yun Liu, Ziqing Wang, Ting Lei

et al.

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(47)

Published: Dec. 15, 2022

Abstract A silver‐promoted decarboxylative annulation of alkynoic acids with 2‐aminopyridines has been developed to assemble 2‐arylimidazo[1,2‐ a ]pyridines. Various functionalities in the aromatic rings two substrates are well tolerated this reaction and gave desired products good yields for broad scope substrates. Additional advantages protocol include mild conditions high regioselectivity. This report represents first example synthesis ]pyridines from acids.

Language: Английский

Citations

2
Copper‐Catalyzed Ring‐Opening (3+2) Annulation of Cyclopropenones with Ketoxime Acetates: Access to 1,2‐Dihydro‐pyrrol‐3‐ones Bearing a Quaternary Carbon Center DOI
Zhen‐Hua Wang, Ping Yang, Yanping Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(18)

Published: April 15, 2022

Abstract A Cu(I)‐catalyzed ring‐opening (3+2) annulation of cyclopropenones with ketoxime acetates has been developed. In disclosed protocol, are selected as C−N splicing unit to participate in the transformation process, furnishing a sequence highly functional 1,2‐dihydro‐pyrrol‐3‐one derivatives good isolated yields. Besides, scale‐up reaction is conducted demonstrate practicability developed methodology and tentative mechanism for also proposed.

Language: Английский

Citations

1