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一种用于多功能3-氨基/羟基噻吩并[3,2-]吡喃水相合成的绿色方法。

A green approach towards the on-water synthesis of multifunctional 3-amino/hydroxy thieno[3,2-]pyrans.

作者信息

Sahu Satya Narayan, Shaw Ranjay, Yadav Saroj, Althagafi Ismail, Upadhyay Manmohan Krishna, Pratap Ramendra

机构信息

Department of Chemistry, Swami Atmanand Govt. English Medium Model College Ambikapur Surguja Chhattisgarh 497001 India.

Department of Chemistry, GLA University Chaumuhan Uttar Pradesh 281406 India.

出版信息

RSC Adv. 2025 Apr 17;15(16):12117-12124. doi: 10.1039/d5ra01296a. eCollection 2025 Apr 16.

DOI:10.1039/d5ra01296a
PMID:40248243
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12004110/
Abstract

An efficient, one-pot, and green synthetic strategy was established for 3-amino/hydroxy thieno[3,2-]pyrans in water through a reaction of 6-aryl-4-(methylthio)-2-oxo-2-pyran-3-carbonitriles/carboxylates with methyl thioglycolate, yielding excellent results (65-95%). The present approach was also employed to synthesize benzo[]thieno[3,2-]chromene-2-carboxylate derivatives in good yield. This efficient method eliminated the need for tedious purification steps, and the products were purified by simply washing the crude material with lukewarm water. Furthermore, the reaction medium was reusable and could be repeated up to six cycles, producing the desired product with only minimal loss, although the reaction time increased with each cycle. All the synthesized compounds were characterized by spectroscopic analysis, and the structure of one compound was confirmed by single-crystal X-ray analysis.

摘要

通过6-芳基-4-(甲硫基)-2-氧代-2-吡喃-3-腈/羧酸盐与巯基乙酸甲酯的反应,在水中为3-氨基/羟基噻吩并[3,2 -]吡喃建立了一种高效、一锅法且绿色的合成策略,产率优异(65 - 95%)。本方法还用于以良好的产率合成苯并[]噻吩并[3,2 -]色烯-2-羧酸盐衍生物。这种高效的方法无需繁琐的纯化步骤,产物只需用温水洗涤粗产物即可纯化。此外,反应介质可重复使用,最多可重复六个循环,尽管反应时间随每个循环增加,但仅产生极小的损失就能得到所需产物。所有合成的化合物均通过光谱分析进行表征,其中一个化合物的结构通过单晶X射线分析得到证实。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/92d4/12004110/7a152308aeeb/d5ra01296a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/92d4/12004110/21717a1472df/d5ra01296a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/92d4/12004110/12a90b125a92/d5ra01296a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/92d4/12004110/7a152308aeeb/d5ra01296a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/92d4/12004110/21717a1472df/d5ra01296a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/92d4/12004110/12a90b125a92/d5ra01296a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/92d4/12004110/7a152308aeeb/d5ra01296a-s2.jpg

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本文引用的文献

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Drug resistance reversal potential of multifunctional thieno[3,2-c]pyran via potentiation of antibiotics in MDR P. aeruginosa.多功能噻吩并[3,2-c]吡喃通过增强多药耐药铜绿假单胞菌中的抗生素逆转耐药潜力。
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Molecular Insights into the Interaction of RONS and Thieno[3,2-c]pyran Analogs with SIRT6/COX-2: A Molecular Dynamics Study.活性氧与噻吩并[3,2-c]吡喃类似物与SIRT6/COX-2相互作用的分子见解:一项分子动力学研究
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Design, synthesis and biological evaluation of 3,5-disubstituted 2-amino thiophene derivatives as a novel class of antitumor agents.
新型抗肿瘤药物3,5-二取代2-氨基噻吩衍生物的设计、合成及生物学评价
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Synthesis and cancer stem cell-based activity of substituted 5-morpholino-7H-thieno[3,2-b]pyran-7-ones designed as next generation PI3K inhibitors.设计为下一代 PI3K 抑制剂的取代 5-吗啉基-7H-噻吩并[3,2-b]吡喃-7-酮的合成及基于癌症干细胞的活性。
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Thieno[3,2-c]pyran-4-one based novel small molecules: their synthesis, crystal structure analysis and in vitro evaluation as potential anticancer agents.噻吩并[3,2-c]吡喃-4-酮类新型小分子的合成、晶体结构分析及其作为潜在抗癌剂的体外评价。
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