Efficient one-pot synthesis of functionalised imidazo[1,2-a]pyridines and unexpected synthesis of novel tetracyclic derivatives by nucleophilic aromatic substitution

Changunda Charles R. K.; Venkatesh B. C.; Mokone William K.; Rousseau Amanda L.; Brady Dean; Fernandes Manuel A.; Bode Moira L.

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Efficient one-pot synthesis of functionalised imidazo[1,2-a]pyridines and unexpected synthesis of novel tetracyclic derivatives by nucleophilic aromatic substitution

机译：通过亲核芳族取代的高效单钾合成官能化咪唑[1,2-A]吡啶和意外合成新型四环衍生物

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Novel tetracyclic imidazo[1,2-a]pyridine derivatives have been prepared by intramolecular nucleophilic aromatic substitution of 5-fluoroimidazo[1,2-a]pyridines under basic conditions. Use of the non-nucleophilic alcoholic solvent tert-butanol, rather than methanol, increased the yield of the tetracycles by reducing the competing intermolecular reaction observed for methanol. In addition, a modified protocol for the dehydration of formamides to isocyanides has been found to be tolerant of an unprotected hydroxyl functional group and one-pot conversion to imidazo[1,2-a]pyridyl-aminocyclohexanol analogues is reported.

机译：通过在基本条件下通过5-氟咪唑[1,2-A]吡啶的分子内亲核芳族取代来制备新的四环素咪唑酯[1,2-A]吡啶衍生物。使用非亲核醇溶剂叔丁醇而不是甲醇，通过减少对甲醇观察到的竞争分子间反应来增加四环的产率。此外，已发现用于甲酰胺的甲酰胺脱水的改性方案是耐受未受保护的羟基官能团的耐受性，并据报道了对咪唑的一锅转化物[1,2-A]吡啶基 - 氨基己醇类似物。

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《RSC Advances》 |2020年第14期|共11页
作者
Changunda Charles R. K.; Venkatesh B. C.; Mokone William K.; Rousseau Amanda L.; Brady Dean; Fernandes Manuel A.; Bode Moira L.;
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Univ Witwatersrand Sch Chem Mol Sci Inst Private Bag 3 PO WITS ZA-2050 Johannesburg South Africa;

Univ Witwatersrand Sch Chem Mol Sci Inst Private Bag 3 PO WITS ZA-2050 Johannesburg South Africa;

Univ Witwatersrand Sch Chem Mol Sci Inst Private Bag 3 PO WITS ZA-2050 Johannesburg South Africa;

Univ Witwatersrand Sch Chem Mol Sci Inst Private Bag 3 PO WITS ZA-2050 Johannesburg South Africa;

Univ Witwatersrand Sch Chem Mol Sci Inst Private Bag 3 PO WITS ZA-2050 Johannesburg South Africa;

Univ Witwatersrand Sch Chem Mol Sci Inst Private Bag 3 PO WITS ZA-2050 Johannesburg South Africa;

Univ Witwatersrand Sch Chem Mol Sci Inst Private Bag 3 PO WITS ZA-2050 Johannesburg South Africa;

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正文语种 eng
中图分类化学;
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1. Efficient one-pot synthesis of functionalised imidazo[1,2-a]pyridines and unexpected synthesis of novel tetracyclic derivatives by nucleophilic aromatic substitution [J] . Changunda Charles R. K., Venkatesh B. C., Mokone William K., RSC Advances . 2020,第14期

机译：通过亲核芳族取代的高效单钾合成官能化咪唑[1,2-A]吡啶和意外合成新型四环衍生物
2. ONE-POT SYNTHESIS OF NEW IMIDAZO[1,2-A]PYRIDINE AND IMIDAZO[1,2-A]PYRIMIDINE DERIVATIVES [J] . Florentina GEORGESCU, Emilian GEORGESCU, Constantin DRAGHICI, Revue roumaine de chimie . 2005,第5期

机译：一锅合成新咪唑并[1,2-A]吡啶和咪唑并[1,2-A]嘧啶衍生物
3. Domino reaction of acyclic alpha,alpha-dialkenoylketene S,S-acetals and diamines: Efficient synthesis of tetracyclic thieno[2,3-b]thiopyran-fused imidazo[1,2-a]pyridine/pyrido[1,2-a]pyrimidines [J] . Liang F, Zhang J, Tan J, Advanced synthesis & catalysis . 2006,第14期

机译：无环α，α-二烯基烯酮S，S-乙缩醛和二胺的多米诺反应：四环噻吩并[2，3-b]硫吡喃稠合的咪唑并[1,2-a]吡啶/吡啶[1,2-a]的高效合成嘧啶类
4. Abnormal nucleophilic reaction of the α-carbon of α,β-unsaturated ester: A Easy Way to Form a Novel Imidazo1,5-a pyridine derivatives [C] . Hongmei Li International symposium for Chinese organic chemists . 2000

机译：α，β-不饱和酯的α-碳的异常亲核反应：形成新型咪唑的简单方法1,5-a吡啶衍生物
5. I. SYNTHETIC APPROACHES TO SUBSTITUTED 2-OXABICYCLO(3.2.1)OCTANE DERIVATIVES AND II. THE SYNTHESIS OF 1-SUBSTITUTED DERIVATIVES OF ANHYDRO (3-CHLOROACETYL-2-HYDROXYIMIDAZO(1,2-A)PYRIDINIUM HYDROXIDE). [D] . FRIEDMAN, ALAN E. 1973

机译：I.取代2-氧杂双环（3.2.1）正己烷衍生物的合成方法和II。合成1-取代的酸酐（3-氯乙酰基-2-羟基咪唑并（1,2-A）吡啶鎓氢氧化物）。
6. Microwave-Induced Nucleophilic 18FFluorination on Aromatic Rings: Synthesis and Effect of Halogen on 18FFluoride Substitution of meta-Halo (F Cl Br I)-Benzonitrile Derivatives [O] . Ning Guo, David Alagille, Gilles Tamagnan, -1

机译：微波诱导的芳香环上的亲核性18F氟化：卤素的合成及其对间位卤代（FClBrI）-苯甲腈衍生物的18F氟化物取代的影响。
7. Efficient one-pot synthesis of functionalised imidazo1,2-apyridines and unexpected synthesis of novel tetracyclic derivatives by nucleophilic aromatic substitution [O] . Charles R. K. Changunda, B. C. Venkatesh, William K. Mokone, 2020

机译：通过亲核芳族取代的高效单钾合成官能化咪唑1,2-A吡啶和意外合成新型四环衍生物

Efficient one-pot synthesis of functionalised imidazo[1,2-a]pyridines and unexpected synthesis of novel tetracyclic derivatives by nucleophilic aromatic substitution

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