Copper-catalyzed oxidative coupling between quinazoline 3-oxides and unactivated aldehydes: an efficient approach to functionalized quinazolines

Fan, Liwen; Wang, Tao; Tian, Ying; Xiong, Fei; Wu, Simei; Liang, Qingjin; Zhao, Junfeng

doi:10.1039/c6cc00946h

Cited by 28 publications

(8 citation statements)

References 58 publications

(4 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the initial step, sodium sulfinate 2b is oxidized by Cu(II) or K 2 S 2 O 8 to form a sulfinate radical A via SET . Then, the intermediate A reacts with quinoline N -oxide 1a through a Minisci-like reaction to generate intermediate B . Radical B is rapidly seized by Cu(I) to give hydroxylamine intermediate C , which is converted into the final product 3ab through elimination of water and regenerates Cu(II) for the next cycle.…”

mentioning

confidence: 99%

Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate

et al. 2016

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The tert‐butylperoxy radical, framed in situ from TBHP, was caught by quinazoline 3‐oxide to shape another O‐focused radical which couples with the acyl radical to produce ester. Further disintegration of the ester generated the cyclic hydroxamic ester [65] . Enantioselective synthesis of molecules are in great utility and hence an intense focus of research area in order to prepare drugs in pure enantiomeric form with good efficacy.…”

Section: C−h Functionalization Of Pyrrolesmentioning

confidence: 99%

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Hunjan

Panday

Gupta

et al. 2021

The Chemical Record

View full text Add to dashboard Cite

Among the known aromatic nitrogen heterocycles, pyrrole represents a privileged aromatic heterocycle ranging its occurrence in the key component of “pigments of life” to biologically active natural products to active pharmaceuticals. Pyrrole being an electron‐rich heteroaromatic compound, its predominant functionalization is legendary to aromatic electrophilic substitution reactions. Although a few excellent reviews on the functionalization of pyrroles including the reports by Baltazzi in 1963, Casiraghi and Rassu in 1995, and Banwell in 2006 are available, they are fragmentary and over fifteen years old, and do not cover the modern aspects of catalysis. A review covering a comprehensive package of direct functionalization on pyrroles via catalytic and non‐catalytic methods including their translational potential is described. Subsequent to statutory yet concise introduction, the classical functionalization on pyrroles using Lewis acids largely following an ionic mechanism is discussed. The subsequent discussion follows the various metal‐catalyzed C−H functionalization on pyrroles, which are otherwise difficult to implement by Lewis acids. A major emphasize is given on the radical based pyrrole functionalization under metal‐free oxidative conditions, which is otherwise poorly highlighted in the literature. Towards the end, the current development of pyrrole functionalization under photocatalyzed and electrochemical conditions is appended. Only a selected examples of substrates and important mechanisms are discussed for different methods highlighting their scopes and limitations. The aromatic nucleophillic substitution on pyrroles (being an electron‐rich heterocycle) happened to be the subject of recent investigations, which has also been covered accentuating their underlying conceptual development. Despite great achievements over the past several years in these areas, many challenges and problems are yet to be solved, which are all discussed in summary and outlook.

show abstract

“…1). 17 The C-4 position of quinazoline 3-oxides was alkylated with ethers in the presence of TBHP. The reaction is performed under metal-free conditions, with moderate to good yields (Scheme 1 , eq.…”

Section: Table 1 Oxidative Cross-coupling Reactions Of 1a Amentioning

confidence: 99%

Mn(OAc)3 Induced C-4 Arylations of Quinazoline 3-Oxides with Arylboronic Acids

2021

View full text Add to dashboard Cite

The use of manganese triacetate as an oxidant component in the C-4 arylations of 2-aryl-quinazoline 3-oxides with arylboronic acids is reported. The new protocol was applied to prepare new 2,4-diarylated quinazoline 3-oxides in good to high yields. The method was shown to tolerate various substituents on both aromatic rings, and no complications as deoxygenation and rearrangement to quinazolin-4(3H)-one was observed.

show abstract

Copper-catalyzed oxidative coupling between quinazoline 3-oxides and unactivated aldehydes: an efficient approach to functionalized quinazolines

Cited by 28 publications

References 58 publications

Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate

Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Mn(OAc)3 Induced C-4 Arylations of Quinazoline 3-Oxides with Arylboronic Acids

Contact Info

Product

Resources

About