Fused thia-heterocycles via isothiocyanates. Part II. A convenient synthesis of some new thieno2,3-bthiopyran-4-one derivatives

Lana Z.El-Agha; Mustafa M.El-Abadelah; Marwan R.KamalSalim S.SabriRanda M.Al-As’adWolfgangVoelter

首页> 外文期刊>Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences >Fused thia-heterocycles via isothiocyanates. Part II. A convenient synthesis of some new thieno2,3-bthiopyran-4-one derivatives

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Fused thia-heterocycles via isothiocyanates. Part II. A convenient synthesis of some new thieno2,3-bthiopyran-4-one derivatives

机译：通过异硫氰酸酯熔融硫杂环。第二部分.一种新型噻吩并2,3-b噻喃-4-酮衍生物的便捷合成

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A facile synthesis of some methyl 5-(arylamino)-4-oxothieno2,3-bthiopyran-6-carboxylates 6a–g is achieved via direct reaction of deprotonated methyl 3-(2,5-dichlorothien-3-yl)-3-oxopropanoate with aryl isothiocyanates in anhydrous tetrahydrofuran (THF) under reflux. Upon saponification of 6a,b, the ester group is eliminated, most logically via decarboxylation of the presumably-formed carboxyl group. Structures of the new compounds 6a–g and 7a,b are supported by microanalytical and spectral NMR, MS electron impact (EI) and HRMS data.

机译：通过去质子化的3-（2,5-二氯噻吩-3-基）-3-氧代丙酸甲酯与芳基异硫氰酸酯在无水四氢呋喃（THF）中的回流直接反应，可以很容易地合成一些5-（芳基氨基）-4-氧代噻吩并[2,3-b]噻喃-6-羧酸甲酯6a–g。在6a，b皂化后，酯基被消除，最合乎逻辑的是通过推测形成的羧基的脱羧。新化合物 6a–g 和 7a，b 的结构得到了微观分析和光谱 [NMR、MS 电子撞击（EI）和 HRMS] 数据的支持。

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来源
《Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences》 |2018年第2期|109-113|共5页
作者
Lana Z.El-Agha; Mustafa M.El-Abadelah; Marwan R.KamalSalim S.SabriRanda M.Al-As’adWolfgangVoelter;
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作者单位

Chemistry Department, Faculty of Science, The University of Jordan, Amman 11942, Jordan;

Department of Chemistry, Faculty of Science, Al-Hussein Bin Talal University, Ma’an 71111, Jordan;

Interfakultäres Institut für Biochemie, Universität Tübingen, Hoppe-Seyler Straße 4, 72076 Tübingen, Germany;

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正文语种英语
中图分类化学;
关键词
aryl isothiocyanates; ester decarboxylation; methyl 3-(2; 5-dichlorothien-3-yl)-3-oxopropanoate; 4-oxothieno2; 3-bthiopyran-6-carboxylates;

机译：芳基异硫氰酸酯;酯脱羧反应;3-（2;5-二氯噻吩-3-基）-3-氧代丙酸酯;4-氧代噻吩并[2;3-b]噻喃-6-羧酸酯;

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1. ChemInform Abstract: Fused Pyridine Bases. New Approach to the Synthesis of 3‐Phenacylbenzobthiophenes and 3‐Phenacyl‐5‐ethylthieno2,3‐bthiophene. Synthesis of New Derivatives of Benzothieno2,3‐cpyrylium and Thieno2′,3′:5,4thieno2,3‐cpyrylium and Pyridine Bases. [J] . S. V. Tolkunov Chem Inform . 1999,第15期

机译：ChemInform Abstract: Fused Pyridine Bases. New Approach to the Synthesis of 3‐Phenacylbenzobthiophenes and 3‐Phenacyl‐5‐ethylthieno2,3‐bthiophene. Synthesis of New Derivatives of Benzothieno2,3‐cpyrylium and Thieno2′,3′:5,4thieno2,3‐cpyrylium and Pyridine Bases.
2. ChemInform Abstract: Nucleosides. Part 3. Reactions of AICA‐Riboside with Isothiocyanates. A Convenient Synthesis of Isoguanosine and Xanthosine Derivatives. [J] . J.‐W. CHERN, G.‐S. LIN, C.‐S. CHENL. B. TOWNSEND Chem Inform . 1991,第46期

机译：ChemInform Abstract: Nucleosides. Part 3. Reactions of AICA‐Riboside with Isothiocyanates. A Convenient Synthesis of Isoguanosine and Xanthosine Derivatives.
3. ChemInform Abstract: Synthesis of Novel Tetraazapentalenes with Fused Cyclic Systems: Reaction of Tetraazapentalene Derivatives with 2‐Bromoethyl and 3‐ Bromopropyl Isothiocyanates. [J] . M. TOMURA, O. MORI, H. CHIKUSAK. INAZUA. ITON. MATSUMURAH. INOUE Chem Inform . 1991,第46期

机译：ChemInform Abstract: Synthesis of Novel Tetraazapentalenes with Fused Cyclic Systems: Reaction of Tetraazapentalene Derivatives with 2‐Bromoethyl and 3‐ Bromopropyl Isothiocyanates.

Fused thia-heterocycles via isothiocyanates. Part II. A convenient synthesis of some new thieno2,3-bthiopyran-4-one derivatives

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