Transition-metal-free solid phase synthesis of 1,2-disubstituted 4-quinolones via the regiospecific synthesis of enaminones

Vinayaka Ajjampura C.; Swaroop Toreshettahally R.; Chikkade Prasanna Kumara; Rangappa Kanchugarakoppal S.; Sadashiva Maralinganadoddi P.

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Transition-metal-free solid phase synthesis of 1,2-disubstituted 4-quinolones via the regiospecific synthesis of enaminones

机译：通过再生合成烯胺酮的过渡 - 无金属固相合成1,2-二取代的4-喹诺酮

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Herein, the transition-metal-free economical solid phase synthesis of 1,2-disubstituted 4-quinolones has been developed via the novel regiospecific synthesis of enaminones. Notably, a wide range of enaminones were synthesized via a silica-supported solid-phase reaction in good to excellent yields. The transformation of enaminones to 1,2-disubstituted 4-quinolones and N-methyl-2-aryl-4-quinolone alkaloid was achieved in high yield via an alumina-supported solid phase reaction. In addition, all the synthesized compounds were isolated directly in their pure form from the reaction mixture using an easy workup procedure.

机译：这里，通过新的烯胺的细节合成来开发1,2-二取代的4-喹诺酮类的过渡 - 金属的经济性固相合成。值得注意的是，通过二氧化硅支持的固相反应合成各种烯酮，其优质为优异的产率。通过氧化铝负载的固相反应，通过氧化铝支持的固相反应高收率实现烯胺酮至1,2-二取代的4喹诺酮和N-甲基-2-芳基-4-喹啉生物碱。此外，使用易于余处步骤，将所有合成的化合物直接以它们的纯形式分离。

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来源
《RSC Advances》 |2016年第14期|共8页
作者
Vinayaka Ajjampura C.; Swaroop Toreshettahally R.; Chikkade Prasanna Kumara; Rangappa Kanchugarakoppal S.; Sadashiva Maralinganadoddi P.;
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Univ Mysore Dept Studies Chem Mysore 570006 Karnataka India;

Univ Mysore Dept Studies Chem Mysore 570006 Karnataka India;

Univ Tokyo Grad Sch Pharmaceut Sci Bunkyo Ku Tokyo 1130033 Japan;

Univ Mysore Dept Studies Chem Mysore 570006 Karnataka India;

Univ Mysore Dept Studies Chem Mysore 570006 Karnataka India;

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中图分类化学;
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1. Transition-metal-free solid phase synthesis of 1,2-disubstituted 4-quinolones via the regiospecific synthesis of enaminones [J] . Vinayaka Ajjampura C., Swaroop Toreshettahally R., Chikkade Prasanna Kumara, RSC Advances . 2016,第14期

机译：通过再生合成烯胺酮的过渡 - 无金属固相合成1,2-二取代的4-喹诺酮
2. Transition-Metal-Free Synthesis of Pyrrolo[1,2-a]pyrazines via Intramolecular Cyclization of N-Propargyl(pyrrolyl)enaminones [J] . Sobenina Lyubov N., Sagitova Elena F., Ushakov Igor A., Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2017,第17期

机译：通过N-炔丙基（吡咯基）烯羟尼酮的分子内环化通过分子内环化过渡 - 无金属的合成吡咯并[1,2-A]吡嗪
3. Solid phase synthesis of 1,6-disubstituted 2,3-diketopiperazines and 1,2-disubstituted piperazines from N-acylated amino acids [J] . Nefzi A., Houghten RA., Giulianotti MA. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 1999,第49期

机译：由N-酰化氨基酸固相合成1,6-二取代的2,3-二酮哌嗪和1,2-二取代的哌嗪
4. Selective Synthesis of 2-Substityted and 1,2-Disubstituted Benzimidazoles [C] . Chengjun Wang, Shanshan Gong, Qi Sun International Conference on Material Engineering, Chemistry, Bioinformatics . 2014

机译：选择性合成2-Coffallated和1,2-二取代的苯并咪唑
5. Synthesis of (1R,2R)-N1,N2-Dibenzylcyclohexane-1,2-diamine as an Auxiliary for a Stereoselective 1,4 Conjugate Addition Reaction; Construction of Polymer Bound (1R,2R)- 1,2-Cyclohexanediamine to evaluate the Solid-Phase Counterpart, and Methodology Development for Synthesis of Functionalized Oligothiophenes. [D] . Poorjahanshah, Homer. 2016

机译：（1R，2R）-N1，N2-二苄基环己烷-1，2-二胺作为立体选择性1，4共轭加成反应的助剂的合成；聚合物结合的（1R，2R）-1,2-环己二胺的构建以评价固相配对物，以及功能化寡聚噻吩的合成方法开发。
6. Magnetic γFe2O3@Sh@Cu2O: an efficient solid-phase catalyst for reducing agent and base-free click synthesis of 14-disubstituted-123-triazoles [O] . Fereshteh Norouzi, Shahrzad Javanshir 2020

机译：磁性γFe2O3@ Sh @ Cu2O：一种高效的固相催化剂用于还原剂和无碱点击合成14-二取代-123-三唑
7. Synthesis and biological evaluation of 1,2-disubstituted 4-quinolone analogues of Pseudonocardia sp. natural products [O] . Stephen M Geddis, Teodora Coroama, Suzanne Forrest, 2018

机译：1,2-二取代的4-喹啉类似物的伪动脉膜SP的合成与生物学评价。天然产品
8. Organolithium Routes to 1,2-Disubstituted Ethylene Derivatives. An Attempted Synthesis of 1,2-Dilithioethylene. [R] . Seyferth, D., Vick, S. C. 1977

机译：有机锂路由到1,2-二取代乙烯衍生物。试图合成1,2-二硫代乙烯。

Transition-metal-free solid phase synthesis of 1,2-disubstituted 4-quinolones via the regiospecific synthesis of enaminones

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