Microwave promoted one-pot preparation of fluorinated propargylamines and their chemical transformation

Chen, Xiaolei; Zhang, Jianmin; Shang, Wenli; Lu, Beiqiong; Jin, Jianan

doi:10.1016/j.jfluchem.2011.08.005

Cited by 24 publications

(12 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(6)]. 20 It can be hence inferred that the synthesis of chalcones from aryl aldehydes and alkynes disclosed herein and the corresponding mechanism are unprecedented. Based on leaching studies, both the indolizine and chalcone syntheses are suggested to proceed under heterogeneous catalysis.…”

Section: Discussionmentioning

confidence: 95%

See 1 more Smart Citation

Synthetic and Mechanistic Studies on the Solvent-Dependent Copper-Catalyzed Formation of Indolizines and Chalcones

2015

View full text Add to dashboard Cite

Copper nanoparticles supported on activated carbon have been found to catalyze the multicomponent synthesis of indolizines from pyridine-2-carbaldehyde derivatives, secondary amines and terminal alkynes in dichloromethane; in the absence of solvent, however, heterocyclic chalcones are formed. We provide compelling evidence that both processes take place through aldehyde-amine-alkyne coupling intermediates. In contrast to other well-known mechanisms for chalcone formation from aldehydes and alkynes, a new reaction pathway is presented involving propargyl amines as intermediates which do not undergo rearrangement. The formation of indolizines or chalcones is driven by inductive and solvent effects, with a wide array of both being reported. In both reactions, the nanoparticulate catalyst has been shown to be

show abstract

Section: Discussionmentioning

confidence: 95%

“…(6)]. 20 It was considered that the nitroaniline moiety acted as a good leaving group, generating allenic cation species which led to the chalcone after reaction with water, in a similar manner as was invoked for propargyl alcohol derivatives [Scheme 1,eq. (3)].…”

mentioning

confidence: 99%

Synthetic and Mechanistic Studies on the Solvent-Dependent Copper-Catalyzed Formation of Indolizines and Chalcones

2015

View full text Add to dashboard Cite

show abstract

“…The novel α-trifluoromethyl chalcones ( 2 – 7 ) and known 1 [ 12 ] , were synthesized from the related chalcones [ 13 , 14 , 15 , 16 ] including novel 10 and 11 , which were obtained by Claisen-Schmidt condensation of aryl methyl ketones and aromatic aldehydes. In target compounds 1 – 7 , the aromatic aldehyde was either unsubstituted or substituted with one of three electron withdrawing groups (F, CF 3 , or NO 2 ) or an electron donating group (NMe 2 ) for comparative purposes.…”

Section: Resultsmentioning

confidence: 99%

α-Trifluoromethyl Chalcones as Potent Anticancer Agents for Androgen Receptor-Independent Prostate Cancer

et al. 2021

View full text Add to dashboard Cite

α-Trifluoromethyl chalcones were prepared and evaluated for their antiproliferative activities against androgen-independent prostate cancer cell lines as well as five additional types of human tumor cell lines. The most potent chalcone 5 showed superior antitumor activity in vivo with both oral and intraperitoneal administration at 3 mg/kg. Cell-based mechanism of action studies demonstrated that 5 induced cell accumulation at sub-G1 and G2/M phases without interfering with microtubule polymerization. Furthermore, several cancer cell growth-related proteins were identified by using chalcone 5 as a bait for the affinity purification of binding proteins.

show abstract

“…Later, Zhang and co-workers synthesized quinolines 132 from aromatic amines 43, aldehydes 2 and phenylacetylene (49) in the presence of CuCl as the catalyst under solvent-free conditions in the oxygen atmosphere and microwave irradiaiton. [81] A series of fluorine-containing quinolines were prepared in 61-85% yields (Scheme 36).…”

Section: Quinolinesmentioning

confidence: 99%

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

2020

View full text Add to dashboard Cite

In recent years, the transition‐metal catalyzed three‐component coupling of an aldehyde, an alkyne and an amine, commonly called A3 coupling has become a powerful tool in organic synthesis. The aim of this review is to give a general overview of A3 coupling utility in the synthesis of heterocycles, highlighting the variety of compounds that can be directly accessed from single reactions. The diverse A3 coupling based methodologies that have been developed for the synthesis of N,O,S‐heterocycles are presented, emphasizing the influence of the reaction conditions and the use of additional reagents in the outcome of the transformations.

show abstract

Microwave promoted one-pot preparation of fluorinated propargylamines and their chemical transformation

Cited by 24 publications

References 19 publications

Synthetic and Mechanistic Studies on the Solvent-Dependent Copper-Catalyzed Formation of Indolizines and Chalcones

Synthetic and Mechanistic Studies on the Solvent-Dependent Copper-Catalyzed Formation of Indolizines and Chalcones

α-Trifluoromethyl Chalcones as Potent Anticancer Agents for Androgen Receptor-Independent Prostate Cancer

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

Contact Info

Product

Resources

About

Microwave promoted one-pot preparation of fluorinated propargylamines and their chemical transformation

Cited by 24 publications

References 19 publications

Synthetic and Mechanistic Studies on the Solvent-Dependent Copper-Catalyzed Formation of Indolizines and Chalcones

Synthetic and Mechanistic Studies on the Solvent-Dependent Copper-Catalyzed Formation of Indolizines and Chalcones

α-Trifluoromethyl Chalcones as Potent Anticancer Agents for Androgen Receptor-Independent Prostate Cancer

A3 Coupling Reaction in the Synthesis of Heterocyclic Compounds

Contact Info

Product

Resources

About

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds