Titanium catalyzed one-pot multicomponent coupling reactions for direct access to substituted pyrimidines

“…In the same year, pyrimidine and its derivatives 33 (51% yield) were achieved by Majumder and Odom by treating amines 31, alkynes 30, and isonitrile 14 in the presence of Ti(NMe 2 ) 2 (dpma) or Ti(dpm)(NMe 2 ) 2 catalysts. 21 The resulting product was condensed with amidine 22 on heating in the presence of tert-amyl alcohol to provide the requisite pyrimidines (Scheme 6). Later, Heravi et al employed the economic, less harmful, and recyclable Keggin-type heteropolyacids (HPAs) for the coupling of 1,3-diketones 34, aldehydes 21, and ammonium acetate 26 to achieve a variety of pyrimidine derivatives in good yields (60%-73%) (Scheme 7).…”

Section: Multicomponent Synthesismentioning

confidence: 99%

Recent synthetic methodologies for pyrimidine and its derivatives

Ibraheem¹,

Saddique²,

Aslam³

et al. 2018

Turk J Chem

View full text Add to dashboard Cite

Pyrimidine derivatives are well known due to their remarkable pharmacological potential in various fields of science, and they are also present in some natural substances like DNA and RNA. These scaffolds manifest diversified biological activities such as antimicrobial, antiinflammatory, anti-HIV, antitubercular, antitumor, antineoplastic, and antimalarial. A pyrimidine ring is constructed when chalcones, amidines, guanidine, nitriles, isocyanates, urea, thiourea, and aminopyrazoles undergo condensation, coupling, or cyclization reactions. In this context, the present review illustrates a variety of novel and efficient synthetic approaches towards the synthesis of pyrimidine and its derivatives that were reported recently.

show abstract

“…On the other hand, the synthetic application of hydroamination with early‐transition‐metal complexes has been largely overlooked. Major contributions to this area have been developed by Odom and co‐workers, who have coupled hydroamination with subsequent reactions to generate hydropyridines,38 pyrroles,39 quinolines,40 pyrimidines41 and pyrazoles,11i and in the synthesis of the natural product withasomnine 11i. Additionally, Doye and co‐workers reported the enantioselective synthesis of (+)‐( S )‐laudanosine and (–)‐( S )‐xylopinine.…”

Section: Applications Of Hydroamination In Synthesismentioning

confidence: 99%

Efficient Anti‐Markovnikov‐Selective Catalysts for Intermolecular Alkyne Hydroamination: Recent Advances and Synthetic Applications

Yim

Schafer

2014

Eur J Org Chem

View full text Add to dashboard Cite

Transition‐metal‐catalyzed hydroamination of alkynes with primary amines is a reliable tool for the synthesis of imines and enamines. Intramolecular hydroamination has been successfully applied in the synthesis of biologically relevant compounds, but intermolecular hydroamination is less commonly employed in synthesis, due to the possible formation of multiple regioisomers. With catalyst control, regioselectivity can be defined. This microreview focuses on recent advances in intermolecular alkyne hydroamination with primary amines in the presence of transition‐metal catalysts that are regioselective for anti‐Markovnikov addition. To highlight their potential use in synthesis, some recently developed methodologies that use intermolecular hydroamination in a tandem sequential manner to generate interesting organic cores are also covered.

show abstract

Titanium catalyzed one-pot multicomponent coupling reactions for direct access to substituted pyrimidines

Cited by 45 publications

References 43 publications

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

Recent synthetic methodologies for pyrimidine and its derivatives

Efficient Anti‐Markovnikov‐Selective Catalysts for Intermolecular Alkyne Hydroamination: Recent Advances and Synthetic Applications

Contact Info

Product

Resources

About