Abdullah Ahmad H, Zahra Jalal A, Sabri Salim S, Awwadi Firas F, Abadleh Mohammed M, Abdallah Qasem M, El-Abadelah Mustafa M
Department of Chemistry, Faculty of Science, The University of Jordan, Amman, 11942, Jordan.
Faculty of Pharmacy, Zarqa University, Zarqa, 13132, Jordan.
Curr Org Synth. 2022 Mar 3;19(2):279-290. doi: 10.2174/1570179418666211109112148.
The preparation of model 6-chloro-5-nitrothieno[2,3-c]pyridazines incorporating (2'-halo-5'-nitrophenyl) entity is described. Interaction of these substrates with N'-(aryl)benzothiohydrazides, in the presence of triethylamine, followed a formal [4+1] annulation, furnishing the respective 1,3,4-thiadiazoline-benzothiazolo [3,2-b]pyridazine hybrids directly. This one-pot synthesis implies thiophene ring-opening and two consecutive intramolecular cyclizations. The structures of the synthesized new hybrids are supported by MS, NMR, and IR spectral data and further confirmed by single-crystal X-ray diffraction. These hybrids exhibit antiproliferative activity with notable selectivity against solid tumor cell lines (IC: 4-18 μM).
This study aimed at exploring the scope and applicability of thiophene ring-opening reaction towards the synthesis of new thiadiazoline-[fused]tricyclic conjugates.
α-Chloro-β-nitrothienopyridazine underwent ring-opening upon reacting with N'-(aryl)benzothiohydrazides generating 1,3,4-thiadiazoline-benzothiazolo[3,2-b]pyridazines.
This new thiophene ring-opening reaction is applied to the one-pot synthesis of thiadiazoline-benzothiazolo[3,2-b]pyridazine couples.
A direct interaction of α-chloro-β-nitrothienopyridazine with N'-(aryl)benzothio-hydrazide at room temperature for 1-2 h occurred.
a-Chloro-β-nitrothieno[2,3-c]pyridazines are suitable substrates for the facile synthesis of thiadiazoline-benzothiazolo[3,2-b]pyridazine hybrids.
This novel ring-opening reaction proceeds via formal [4+1] annulation and provides a versatile approach to various conjugated and/or fused five-membered heterocycles.
本文描述了含（2'-卤-5'-硝基苯基）基团的6-氯-5-硝基噻吩并[2,3-c]哒嗪模型的制备。在三乙胺存在下，这些底物与N'-（芳基）苯并硫代酰肼相互作用，进行形式上的[4+1]环化反应，直接生成相应的1,3,4-噻二唑啉-苯并噻唑并[3,2-b]哒嗪杂化物。这种一锅法合成涉及噻吩环开环和两个连续的分子内环化反应。合成的新杂化物的结构通过质谱、核磁共振和红外光谱数据得到支持，并通过单晶X射线衍射进一步确认。这些杂化物表现出抗增殖活性，对实体瘤细胞系具有显著的选择性（IC：4-18 μM）。
本研究旨在探索噻吩环开环反应在合成新型噻二唑啉-[稠合]三环共轭物方面的范围和适用性。
α-氯-β-硝基噻吩并哒嗪与N'-（芳基）苯并硫代酰肼反应时发生环开环，生成1,3,4-噻二唑啉-苯并噻唑并[3,2-b]哒嗪。
将这种新的噻吩环开环反应应用于一锅法合成噻二唑啉-苯并噻唑并[3,2-b]哒嗪偶联物。
α-氯-β-硝基噻吩并哒嗪与N'-（芳基）苯并硫代酰肼在室温下直接相互作用1-2小时。
α-氯-β-硝基噻吩并[2,3-c]哒嗪是简便合成噻二唑啉-苯并噻唑并[3,2-b]哒嗪杂化物的合适底物。
这种新型环开环反应通过形式上的[4+1]环化进行，为各种共轭和/或稠合五元杂环提供了一种通用方法。
