Reaction of 3-(R-methylidene)-2-ethoxylindolenines with N,N'-binucleophiles

Borovik, V. P.; Gatilov, Yu. V.; Shkurko, O. P.

doi:10.1134/s1070428016020123

Cited by 2 publications

(1 citation statement)

References 15 publications

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“…On the other hand, selective O-alkylation can take place under certain conditions, although the occurrence of this reaction in the scientific literature is very rare. It can only be carried out using special alkylating agents, e.g., trialkyloxonium tetrafluoroborates [38,39,40,41,42,43,44,45,46]. …”

Section: Introductionmentioning

confidence: 99%

Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles. Practical Synthesis of N-Unprotected 3,3-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring

2016

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The paper provides a comprehensive review of the base-catalysed C3-alkylation of N-unprotected-3-monosubstituted oxindoles. Based on a few, non-systematic studies described in the literature using butyllithium as the deprotonating agent, an optimized method has now been elaborated, via the corresponding lithium salt, for the selective C3-alkylation of this family of compounds. The optimal excess of butyllithium and alkylating agent, and the role of the halogen atom in the latter (alkyl bromides vs. iodides) were also studied. The alkylation protocol has also been extended to some derivatives substituted at the aromatic ring. Finally, various substituents were introduced into the aromatic ring of the N-unprotected 3,3-dialkyloxindoles obtained by this optimized method.

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Section: Introductionmentioning

confidence: 99%

Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles. Practical Synthesis of N-Unprotected 3,3-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring

2016

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Four-Component Synthesis of 9H-Pyrimido[4,5-b]indoles Using Ammonium Iodide as the Nitrogen Source

et al. 2023

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A four-component synthesis of 2-phenyl-9H-pyrimido[4,5-b]indoles was developed using indole-3-carboxaldehydes, aromatic aldehyde and ammonium iodide as the raw materials under transition-metal-free conditions. The pyrimidine ring was formed in one pot through [4+2] annulation reaction. Four C–N bonds were formed in one pot promoted by iodine and iodide additives. This work is highlighted by using two ammonium iodides as the sole nitrogen source.

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Reaction of 3-(R-methylidene)-2-ethoxylindolenines with N,N'-binucleophiles

Cited by 2 publications

References 15 publications

Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles. Practical Synthesis of N-Unprotected 3,3-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring

Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles. Practical Synthesis of N-Unprotected 3,3-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring

Four-Component Synthesis of 9H-Pyrimido[4,5-b]indoles Using Ammonium Iodide as the Nitrogen Source

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