Thiophene ring-opening reactions VI. Attempted cyclization towards [fused]-tricyclic system involving a thiolate anion and suitably located electrophilic carbon-Reference-Cited by-同舟云学术

Thiophene ring-opening reactions VI. Attempted cyclization towards [fused]-tricyclic system involving a thiolate anion and suitably located electrophilic carbon

Published:2022-08-08 Issue:3-4 Volume:78 Page:133-140
ISSN:0939-5075
Container-title:Zeitschrift für Naturforschung C
language:en
Short-container-title:

Author:

Abdullah Ahmad H.¹²,Zahra Jalal A.¹,Sabri Salim S.¹,Awwadi Firas F.¹,Hussein Ahmad Q.¹,El-Abadelah Mustafa M.¹

Affiliation:

1. Chemistry Department , Faculty of Science, The University of Jordan , Amman 11942 , Jordan

2. Faculty of Pharmacy, Zarqa University , Zarqa 13132 , Jordan

Abstract

Abstract Model α-chloro-β-nitrothieno[2,3-c]pyridazines incorporating N1-(aryl) entity appended with ortho-methoxycarbonyl or trifluoromethyl group were prepared via intramolecular cyclization of their respective N-arylhydrazone precursors. Interaction of these substrates with N′-(p-fluorophenyl)benzothiohydrazide, in the presence of NEt3, furnished the respective 1,3,4-thiadiazoline–pyridazine thiolate hybrids that were S-methylated to produce the corresponding “sulfanyl” derivatives. Their structures were deduced from spectral data, and confirmed by single-crystal X-ray diffraction.

Funder

The University of Jordan, Amman, Jordan

Publisher

Walter de Gruyter GmbH

Subject

General Biochemistry, Genetics and Molecular Biology

Link

https://www.degruyter.com/document/doi/10.1515/znc-2022-0080/pdf

Reference18 articles.

1. Abadleh, MM, Abdullah, AH, Awwadi, FF, El-Abadelah, MM. Thiophene ring-opening reactions. Direct access to the synthesis of 1,3,4-thiadiazoline-(condensed) pyridone hybrids. Tetrahedron 2021;83:131957. https://doi.org/10.1016/j.tet.2021.131957.

2. Abdullah, A, Zahra, J, Sabri, S, Awwadi, F, Abadleh, M, Abdallah, Q, et al.. Thiophene ring-opening reactions III. One-pot synthesis and antitumor activity of 1,3,4-thiadiazoline–benzothiazolo[3,2-b]pyridazine hybrids. Curr Org Synth 2022;19:279–90. https://doi.org/10.2174/1570179418666211109112148.

3. El-Abadelah, MM, Kamal, MR, Tokan, WM, Jarrar, SO. Synthesis and properties of 1-aryl-6-chloro-1,4-dihydro-4-oxothieno[2,3-c]pyridazine-3-carboxylic acids. J Prakt Chem Chem Ztg 1997;339:284–7. https://doi.org/10.1002/prac.19973390150.

4. Abadleh, MM, Arafat, T, Abu-qatouseh, L, El-Abadelah, MM, Voelter, W. Facile synthesis of model 2,4-diaryl-1,3,4-thiadiazino[5,6-h]fluoroquinolones. Z Naturforsch B Chem Sci 2019;74:507–12. https://doi.org/10.1515/znb-2019-0023.

5. CrysAlisPro 1.171.41.104a; Rigaku OD, 2021.