Continuous-flow synthesis of 3,5-disubstituted pyrazoles via sequential alkyne homocoupling and Cope-type hydroamination

Oetvoes Sandor B.; Georgiades Adam; Ozsvar Daniel; Fulop Ferenc

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Continuous-flow synthesis of 3,5-disubstituted pyrazoles via sequential alkyne homocoupling and Cope-type hydroamination

机译：通过顺序炔烃同性化和COPE型水醋酸连续合成3,5-二取代的吡唑胺

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A flow chemistry-based approach is presented for the synthesis of 3,5-disubstituted pyrazoles via sequential copper-mediated alkyne homocoupling and Cope-type hydroamination of the intermediary 1,3-diynes in the presence of hydrazine as nucleophilic reaction partner. The proposed multistep methodology offers an easy and direct access to valuable pyrazoles from cheap and readily available starting materials and without the need for the isolation of any intermediates.

机译：通过顺序铜介导的炔烃同性化和中间体1,3-脱酰胺的含水剂作为亲核反应合作乳糖的存在，通过顺序铜介导的炔烃合成3,5-二取代的吡唑来合成3,5-二取代的吡唑。建议的多步骤方法提供了一种简单直接地直接访问廉价和容易获得的起始材料的宝贵吡唑，而无需孤立任何中间体。

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《RSC Advances》 |2019年第15期|共7页
作者
Oetvoes Sandor B.; Georgiades Adam; Ozsvar Daniel; Fulop Ferenc;
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Univ Szeged Interdisciplinary Excellence Ctr Inst Pharmaceut Chem Eotvos U 6 H-6720 Szeged Hungary;

Univ Szeged Interdisciplinary Excellence Ctr Inst Pharmaceut Chem Eotvos U 6 H-6720 Szeged Hungary;

Univ Szeged Interdisciplinary Excellence Ctr Inst Pharmaceut Chem Eotvos U 6 H-6720 Szeged Hungary;

Univ Szeged Interdisciplinary Excellence Ctr Inst Pharmaceut Chem Eotvos U 6 H-6720 Szeged Hungary;

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正文语种 eng
中图分类化学;
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1. Continuous-flow synthesis of 3,5-disubstituted pyrazoles via sequential alkyne homocoupling and Cope-type hydroamination [J] . Oetvoes Sandor B., Georgiades Adam, Ozsvar Daniel, RSC Advances . 2019,第15期

机译：通过顺序炔烃同性化和COPE型水醋酸连续合成3,5-二取代的吡唑胺
2. Synthesis of 3,5-disubstituted pyrazoles via cope-type hydroamination of 1,3-dialkynes [J] . Wang L., Yu X., Feng X., The Journal of Organic Chemistry . 2013,第4期

机译：上交型加氢1,3-二炔的合成3,5-二取代的吡唑
3. Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations [J] . Bassaco Mariana M., Fortes Margiani P., Kaufman Teodoro S., RSC Advances . 2015,第27期

机译：使用两次连续的胺化反应由1,3-二炔-吲哚衍生物无金属合成3,5-二取代的1H-和1-芳基-1H-吡唑
4. Synthesis and Biological Activity of a 3,5-Disubstituted-1,2,4-Oxadiazole Fungicide Containing 3-Pyrazole Group [C] . Mingming Zhang, Huanqi Cui, Junjun Han, 2019 4th International Conference on Life Sciences, Medicine, and Health（ 2019年第四届生命科学、医学和健康国际会议）（ICLSMH 2019）论文集 . -1

机译：3,5-二取代的-1,2,4-二唑胺含3-吡唑基团的合成和生物活性
5. Intramolecular Cope-Type Hydroamination of Alkenes in the Synthesis of Alkaloids: Total Synthesis of (+/-)-Coniine and (+/-)-Desbromoarborescidine A and Studies on a Novel Amination Strategy Towards Manzamine A. [D] . Dion, Isabelle. 2012

机译：生物碱合成中烯烃的分子内Cope型加氢胺化：（+/-）-丝氨酸和（+/-）-去溴基硼烷甲酰胺A的全合成以及对Manzamine A的新型胺化策略的研究。
6. A Cationic Gold(I) Complex as a General Catalyst for the Intermolecular Hydroamination of Alkynes. Application to the One-Pot Synthesis of Allenes from Two Alkynes and a Sacrificial Amine [O] . Xiaoming Zeng, Guido D. Frey, Shazia Kousar, -1

机译：阳离子金（I）配合物作为炔烃分子间加氢胺化反应的一般催化剂。由两个炔烃和一种牺牲胺一锅法合成烯丙基的应用
7. Synthesis of some 1-aryl-3,5-disubstituted-pyrazoles by N-arylation of 3,5-disubstituted-pyrazoles with 4-fluoro and 2-fluoronitrobenzene under microwave irradiation and classical heating [O] . Ibrahim Bouabdallah, Rachid Touzani, Ismail Zidane, 2006

机译：在微波辐射和经典加热下，通过3,5-二取代吡唑与4-氟和2-氟硝基苯的N-芳基化合成一些1-芳基-3,5-二取代吡唑
8. Synthesis and Properties of a New Explosive, 4-Amino-3,5-Dinitro-1H-Pyrazole (LLM-116) [R] . Schmidt, R. D., Lee, G. S., Pagoria, P. F., 2001

机译：新型炸药4-氨基-3,5-二硝基-1H-吡唑（LLm-116）的合成与性质

Continuous-flow synthesis of 3,5-disubstituted pyrazoles via sequential alkyne homocoupling and Cope-type hydroamination

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