The kinetics of the reactions of a series of reference carbon nucleophiles, consisting of N-methylpyrrole A, indole B, N-methylindole C, and enamines D−G, with 10 electron-deficient aromatic and heteroaromatic substrates (1−10), resulting in the formation of stable anionic σ-adducts, have been investigated in acetonitrile at 20 °C. It is shown that the second-order rate constants k1 pertaining to the carbon−carbon coupling step of these processes fit nicely the three-parameter equation log k (20 °C) = s(N + E), allowing the determination of the electrophilicity parameters E of 1−10 and therefore the ranking of these neutral electron-deficient compounds on the comprehensive electrophilicity scale defined for cationic electrophiles by Mayr et al. (Mayr, H.; Kempf, B,; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66). The E values of 1−10 are found to cover a range from −13 to −5, going from 1,3,5-trinitrobenzene 1, the least reactive molecule, to 4,6-dinitrotetrazolo[1,5-a]pyridine 8, 4-nitro-6-trifluoromethanesu...

Ranking the Reactivity of Superelectrophilic Heteroaromatics on the Electrophilicity Scale

Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides.

Xanthane sesquiterpenoids: structure, synthesis and biological activity

SBA-15/PrN(CH2PO3H2)2 as a novel and efficient mesoporous solid acid catalyst with phosphorous acid tags and its application on the synthesis of new pyrimido[4,5-b]quinolones and pyrido[2,3-d]pyrimidines via anomeric based oxidation

The chapter reviews the classic Reissert reaction, the keystone of a broad family of multicomponent reactions involving azines, electrophilic reagents and nucleophiles to yield N,α-disubstituted dihydroazine adducts. The first sections deal with the standard nucleophilic attack upon activated azines, including asymmetric transformations. Section 5 focuses on the generation of dipolar intermediates by azine activation, and on their subsequent transformation; chiefly in cycloadditions. Lastly, Sect. 6 is primarily devoted to a special branch of this chemistry involving isocyanides. It also covers the reactivity of dihydroazines and reviews the mechanistic proposals for related reactions.

Recent Developments in Reissert-Type Multicomponent Reactions

Bis(trimethylsilyl)ketene Acetals as C,O-Dinucleophiles: One-Pot Formation of Polycyclic γ- and δ-Lactones from Pyridines and Pyrazines

Double nucleophilic addition of bis(trimethylsilyl)ketene acetals to carbon-carbon double bonds of pyrazines : formation of polycyclic γ-lactones

Triple nucleophilic additions of (trimethylsilyl)ketene acetals to tropylium derivatives: access to the core nuclei of xanthanolides

Lactones from lactones: regio and diastereoselective double dinucleophilic additions of bis(OTMS) ketene acetals to pyridines

Corrigendum to “Triple nucleophilic additions of (trimethylsilyl)ketene acetals to tropylium derivatives: access to the core nuclei of xanthanolides”: [Tetrahedron Lett. 45 (2004) 2409]

Yiming Xu

Papers

Bis(trimethylsilyl)ketene Acetals as C,O-Dinucleophiles: One-Pot Formation of Polycyclic γ- and δ-Lactones from Pyridines and Pyrazines

Double nucleophilic addition of bis(trimethylsilyl)ketene acetals to carbon-carbon double bonds of pyrazines : formation of polycyclic γ-lactones

Triple nucleophilic additions of (trimethylsilyl)ketene acetals to tropylium derivatives: access to the core nuclei of xanthanolides

Lactones from lactones: regio and diastereoselective double dinucleophilic additions of bis(OTMS) ketene acetals to pyridines

Corrigendum to “Triple nucleophilic additions of (trimethylsilyl)ketene acetals to tropylium derivatives: access to the core nuclei of xanthanolides”: [Tetrahedron Lett. 45 (2004) 2409]