scholarly journals Diastereoselective addition to N-acyliminium ions with aryl- and alkenyl boronic acids via a Petasis-type reaction

RSC Advances ◽  
2012 ◽  
Vol 2 (6) ◽  
pp. 2266 ◽  
Author(s):  
Satoshi Mizuta ◽  
Osamu Onomura
Keyword(s):  
Boronic Acids ◽  
Type Reaction ◽  
Acyliminium Ions ◽  
Diastereoselective Addition

The intramolecular tandem Michael/Mannich-type reaction of α,β-unsaturated carbonyl compounds with acyliminium ions provides access to chiral indolizidines

2007 ◽  
Vol 18 (13) ◽  
pp. 1533-1539 ◽  
Author(s):  
Yuji Koseki ◽  
Koji Fujino ◽  
Ai Takeshita ◽  
Hiroto Sato ◽  
Tatsuo Nagasaka
Keyword(s):  
Carbonyl Compounds ◽  
Type Reaction ◽  
Acyliminium Ions

Synthesis of Pyrimido[2,1-a]isoindolone and Isoindolo[2,1-a]quinazolinone via Intramolecular Aza-Prins Type Reaction

2021 ◽  
Author(s):  
Anil Saikia ◽  
Subhamoy Biswas ◽  
Bikoshita Porashar ◽  
Pallav Jyoti Arandhara
Keyword(s):  
Cyclization Reaction ◽  
Type Reaction ◽  
Acyliminium Ions

A novel aza-Prins type cyclization reaction involving N-acyliminium ions and amides is reported for the synthesis of tetrahydropyrimido[2,1-a]isoindole-2,6-dione and 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives in excellent yields. The strategy features inexpensive reagents, mild...

scholarly journals Efficient Access to 3,5-Disubstituted 7-(Trifluoromethyl)pyrazolo[1,5-a]pyrimidines Involving SNAr and Suzuki Cross-Coupling Reactions

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2062 ◽  
Author(s):  
Badr Jismy ◽  
Abdellatif Tikad ◽  
Mohamed Akssira ◽  
Gérald Guillaumet ◽  
Mohamed Abarbri
Keyword(s):  
Kinase Inhibitors ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Starting Material ◽  
Coupling Reactions ◽  
Synthetic Methodology ◽  
Type Reaction ◽  
Cross Coupling Reactions ◽  
Pim1 Kinase ◽  
Efficient Access

An efficient and original synthesis of various 3,5-disubstituted 7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidines is reported. A library of compounds diversely substituted in C-3 and C-5 positions was easily prepared from a common starting material, 3-bromo-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-one. In C-5 position, a SNAr type reaction was achieved by first activating the C–O bond of the lactam function with PyBroP (Bromotripyrrolidinophosphonium hexafluorophosphate), followed by the addition of amine or thiol giving monosubstituted derivatives, whereas in C-3 position, arylation was performed via Suzuki–Miyaura cross-coupling using the commercially available aromatic and heteroaromatic boronic acids. Moreover, trifluoromethylated analogues of potent Pim1 kinase inhibitors were designed following our concise synthetic methodology.

scholarly journals Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Kai Yang ◽  
Feng Zhang ◽  
Tongchang Fang ◽  
Chaokun Li ◽  
Wangyang Li ◽  
...  
Keyword(s):  
Work Engagement ◽  
Multicomponent Reactions ◽  
Functional Group ◽  
Coupling Reaction ◽  
Boronic Acids ◽  
Molecular Scaffolds ◽  
Type Reaction ◽  
Carbon Nucleophiles ◽  
Mild Conditions ◽  
Operational Simplicity

AbstractMulticomponent reactions (MCRs) facilitate the rapid and diverse construction of molecular scaffolds with modularity and step economy. In this work, engagement of boronic acids as carbon nucleophiles culminates in a Passerini-type three-component coupling reaction towards the synthesis of an expanded inventory of α-hydroxyketones with skeletal diversity. In addition to the appealing features of MCRs, this protocol portrays good functional group tolerance, broad substrate scope under mild conditions and operational simplicity. The utility of this chemistry is further demonstrated by amenable modifications of bioactive products and pharmaceuticals as well as in the functionalization of products to useful compounds.

Direct introduction of a naphthalene-1,8-diamino boryl [B(dan)] group by a Pd-catalysed selective boryl transfer reaction

2015 ◽  
Vol 51 (26) ◽  
pp. 5656-5659 ◽  
Author(s):  
Liang Xu ◽  
Pengfei Li
Keyword(s):  
Transfer Reaction ◽  
Boronic Acids ◽  
Reaction Conditions ◽  
Direct Introduction ◽  
Type Reaction ◽  
Aryl Bromides

Under Palladium-catalysed Miyaura-type reaction conditions, a non-symmetrical diboron reagent, B(pin)-B(dan), was found to selectively deliver the B(dan) moiety to aryl bromides and chlorides. This method represents a direct and efficient way to masked boronic acids and boron-differentiated di- and polyboron compounds.

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