A General and Efficient Route to Thionoesters via Thionoacyl Nitrobenzotriazoles

Shalaby, M. Ashraf; Rapoport, Henry

doi:10.1021/jo981985u

Cited by 23 publications

(13 citation statements)

References 40 publications

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“…1H-Benzotriazole-1-yl alkyl carbonates (120) are convenient and inexpensive coupling agents in the preparation of active esters for the synthesis of amides [174]. A general and efficient route to thionoesters via thionoacyl nitrobenzotriazoles 121 has been reported [175]. The Vilsmeier-type reagent 122 with b-enaminonitriles provides a regioselective route to the preparation of nicotinonitriles [176] and was employed in the direct and efficient synthesis of dimethylformamidrazones from hydrazines [177].…”

Section: Benzotriazole-mediated Imidoylationmentioning

confidence: 99%

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

Yet

2011

Modern Heterocyclic Chemistry

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Section: Benzotriazole-mediated Imidoylationmentioning

confidence: 99%

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

Yet

2011

Modern Heterocyclic Chemistry

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“…The DAG-lactone targets devoid of the sn-1 carbonyl (E-9 and Z-10) were synthesized, respectively, from the isomers E- (21) and Z- (22), 19 which were prepared according to our published method (Scheme 3). Removal of the benzyl ether with BCl 3 at −78 °C gave the corresponding monoalcohols E-23 and Z-24, which were subsequently converted to the corresponding methylsulfonate esters E-25 and Z-26.…”

Section: Chemistrymentioning

confidence: 99%

Conformationally Constrained Analogues of Diacylglycerol (DAG). 25. Exploration of the sn-1 and sn-2 Carbonyl Functionality Reveals the Essential Role of the sn-1 Carbonyl at the Lipid Interface in the Binding of DAG-Lactones to Protein Kinase C

Kang

Peach

et al. 2005

J. Med. Chem.

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Diacylglycerol (DAG) lactones with altered functionality (C=O --> CH(2) or C=O --> C=S) at the sn-1 and sn-2 carbonyl pharmacophores were synthesized and used as probes to dissect the individual role of each carbonyl in the binding to protein kinase C (PKC). The results suggest that the hydrated sn-1 carbonyl is engaged in very strong hydrogen-bonding interactions with the charged lipid headgroups and organized water molecules at the lipid interface. Conversely, the sn-2 carbonyl has a more modest contribution to the binding process as a result of its involvement with the receptor (C1 domain) via conventional hydrogen bonding to the protein. The parent DAG-lactones, E-6 and Z-7, were designed to bind exclusively in the sn-2 binding mode to ensure the correct orientation and disposition of pharmacophores at the binding site.

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“…33,34 In addition, LR has a foul-smelling odor and a narrow substrate scope for the functionalization of esters containing conjugated electron-withdrawing groups. 35 In 2005, the Katritzky group showed that thionoesters can be synthesized from thiocarbonylbenzotriazoles serving as substrates (Scheme 2c). 36 However, this protocol was encumbered by the hard-to-get reactant and the use of expensive reagents.…”

Section: Introductionmentioning

confidence: 99%