Thiophene Ring-Opening Reactions III: One-Pot Synthesis and Antitumor Activity of 1,3,4-Thiadiazoline–Benzothiazolo[3,2-b]pyridazine Hybrids

Introduction: 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 (IC50: 4-18 μM). Aims: This study aimed at exploring the scope and applicability of thiophene ring-opening reaction towards the synthesis of new thiadiazoline–[fused]tricyclic conjugates. Background: α-Chloro-β-nitrothienopyridazine underwent ring-opening upon reacting with N'-(aryl)benzothiohydrazides generating 1,3,4-thiadiazoline–benzothiazolo[3,2-b]pyridazines. Objective: This new thiophene ring-opening reaction is applied to the one-pot synthesis of thiadiazoline–benzothiazolo[3,2-b]pyridazine couples. Method: A direct interaction of α-chloro-β-nitrothienopyridazine with N'-(aryl)benzothiohydrazide at room temperature for 1-2 h occurred. Result: α-Chloro-β-nitrothieno[2,3-c]pyridazines are suitable substrates for the facile synthesis of thiadiazoline–benzothiazolo[3,2-b]pyridazine hybrids. Conclusion: 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.

Download Full-text

An Overview of the One-pot Synthesis of Imidazolines

Current Organic Chemistry ◽

10.2174/1385272824999201001153735 ◽

2020 ◽

Vol 24 (20) ◽

pp. 2341-2355

Author(s):

Thaipparambil Aneeja ◽

Sankaran Radhika ◽

Mohan Neetha ◽

Gopinathan Anilkumar

Keyword(s):

Asymmetric Catalysis ◽

Organic Compounds ◽

Ring Opening ◽

Ecological Impact ◽

Chiral Auxiliary ◽

One Pot ◽

One Pot Synthesis ◽

The One ◽

Synthetic Intermediate ◽

Heterocyclic Moiety

One-pot syntheses are a simple, efficient and easy methodology, which are widely used for the synthesis of organic compounds. Imidazoline is a valuable heterocyclic moiety used as a synthetic intermediate, chiral auxiliary, chiral catalyst and a ligand for asymmetric catalysis. Imidazole is a fundamental unit of biomolecules that can be easily prepared from imidazolines. The one-pot method is an impressive approach to synthesize organic compounds as it minimizes the reaction time, separation procedures, and ecological impact. Many significant one-pot methods such as N-bromosuccinimide mediated reaction, ring-opening of tetrahydrofuran, triflic anhydrate mediated reaction, etc. were reported for imidazoline synthesis. This review describes an overview of the one-pot synthesis of imidazolines and covers literature up to 2020.

Download Full-text

One-Pot Synthesis of Novel Dibenzoxanthenes, Diarylbutanes, and Calix[4]resorcinarenes via Consecutive Pyrrolidine Ring-Closure/Ring-Opening Reactions

Journal of Chemistry ◽

10.1155/2019/3424319 ◽

2019 ◽

Vol 2019 ◽

pp. 1-7

Author(s):

Andrey V. Smolobochkin ◽

Almir S. Gazizov ◽

Alexander R. Burilov ◽

Michail A. Pudovik

Keyword(s):

Ring Opening ◽

Ring Closure ◽

Acidic Media ◽

Pyrrolidine Ring ◽

One Pot ◽

One Pot Synthesis ◽

Ring Opening Reactions

Herein, we report the approach to the otherwise hardly accessible dibenzoxanthenes, diarylbutanes, and calix[4]resorcinarenes possessing urea moieties based on the reaction of N-(4,4-diethoxybutyl)ureas with electron-rich aromatics in strongly acidic media. Unlike the previously developed methods, the proposed approach benefits from one-pot procedure and allows to obtain the target compounds with much higher yields.

Download Full-text

A straightforward one-pot synthesis of biologically important imidazolyl alcohols via catalytic epoxide ring-opening reactions

Tetrahedron Letters ◽

10.1016/j.tetlet.2012.04.019 ◽

2012 ◽

Vol 53 (24) ◽

pp. 3049-3051 ◽

Cited By ~ 9

Author(s):

M. Abdul Jalil ◽

Shah Md. Masum

Keyword(s):

Ring Opening ◽

Epoxide Ring ◽

One Pot ◽

Epoxide Ring Opening ◽

One Pot Synthesis ◽

Ring Opening Reactions

Download Full-text

Reaction of isatins with 6-amino uracils and isoxazoles: isatin ring-opening vs. annulations and regioselective synthesis of isoxazole fused quinoline scaffolds in water

Green Chemistry ◽

10.1039/c5gc00006h ◽

2015 ◽

Vol 17 (6) ◽

pp. 3362-3372 ◽

Cited By ~ 29

Author(s):

Nataraj Poomathi ◽

Sivakalai Mayakrishnan ◽

Doraiswamy Muralidharan ◽

Rajagopal Srinivasan ◽

Paramasivan T. Perumal

Keyword(s):

Ring Opening ◽

Sulphonic Acid ◽

Regioselective Synthesis ◽

One Pot ◽

One Pot Synthesis ◽

The One ◽

Straightforward Approach

A straightforward approach for the one-pot synthesis of isoxazoloquinoline and spiroxindole derivatives in water has been established using p-toluene sulphonic acid as a catalyst.

Download Full-text

Mild and efficient one-pot synthesis of chiral β-chalcogen amides via 2-oxazoline ring-opening reaction mediated by indium metal

Journal of Organometallic Chemistry ◽

10.1016/j.jorganchem.2008.08.031 ◽

2008 ◽

Vol 693 (24) ◽

pp. 3563-3566 ◽

Cited By ~ 13

Author(s):

Antonio L. Braga ◽

Fábio Z. Galetto ◽

Paulo S. Taube ◽

Márcio W. Paixão ◽

Claudio C Silveira ◽

...

Keyword(s):

Ring Opening ◽

One Pot ◽

One Pot Synthesis ◽

Ring Opening Reaction ◽

Indium Metal

Download Full-text

Efficient one-pot synthesis of β-hydroxyphosphonates: regioselective nucleophilic ring opening reaction of epoxides with triethyl phosphite catalyzed by Al(OTf)3

Tetrahedron ◽

10.1016/j.tet.2009.06.106 ◽

2009 ◽

Vol 65 (36) ◽

pp. 7691-7695 ◽

Cited By ~ 19

Author(s):

Sara Sobhani ◽

Asieh Vafaee

Keyword(s):

Ring Opening ◽

Triethyl Phosphite ◽

One Pot ◽

One Pot Synthesis ◽

Ring Opening Reaction ◽

Nucleophilic Ring Opening

Download Full-text

Thiophene ring-opening reactions IV. Facile generation of novel ethyl 4-hydroxy-6-thioxonicotinate─1,3,4- thiadiazoline hybrids

Letters in Organic Chemistry ◽

10.2174/1570178618666211110141423 ◽

2021 ◽

Vol 18 ◽

Author(s):

Mohammed M. Abadleh ◽

Ahmad H. Abdullah ◽

Jalal A. Zahra ◽

Salim S. Sabri ◽

Firas F. Awwadi ◽

...

Keyword(s):

Single Crystal ◽

Spectral Data ◽

1H Nmr ◽

13C Nmr ◽

Ring Opening ◽

Thiophene Ring ◽

X Ray Diffraction ◽

X Ray ◽

Mild Conditions ◽

Ring Opening Reactions

: A set of triethylammonium 4-oxo-6-pyridinethiolate–1,3,4-thiadiazoline hybrids (3a-e) were prepared via the reaction of ethyl 2-chloro-6-cyclopropyl-3- nitro-4-oxothieno[2,3-b]pyridine- 5-carboxylate (2) with the appropriate thiobenzoyl- hydrazide (1a-e) in acetonitrile and triethylamine. These hybrids were readily converted, under neutral mild conditions, into the corresponding 4-hydroxy-6-thioxopyridine –thiadiazoline hybrids (5a-e). The structures of the latter set are supported by HRMS, 1H NMR and 13C NMR spectral data and further confirmed by single-crystal X-ray diffraction studies. Alkylation of these hybrids in the presence of triethylamine occurred exclusively at the 6-thioxosulfur, yielding the respective 6-sulfanyl derivatives (6a-c).

Download Full-text

One-Pot Synthesis of B-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions

Catalysts ◽

10.3390/catal10111348 ◽

2020 ◽

Vol 10 (11) ◽

pp. 1348

Author(s):

Sergey A. Anufriev ◽

Akim V. Shmal’ko ◽

Kyrill Yu. Suponitsky ◽

Igor B. Sivaev

Keyword(s):

Functional Groups ◽

X Ray Diffraction ◽

One Pot ◽

One Pot Synthesis ◽

Palladium Catalyzed ◽

Catalyzed Reactions ◽

The One ◽

Solid State Structures ◽

Derivatives Of

The simple and efficient method was developed for the one-pot synthesis of B-substituted aryl derivatives of ortho-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-ortho-carborane and generated in situ organozinc compounds. The method proposed was used to prepare a series of 9-aryl-ortho-carboranes, including those containing nitrile and ester groups, 9-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, o-OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, and p-COOEt). It was demonstrated that the same approach can be used for synthesis of diaryl derivatives of ortho-carborane 9,12-(RC6H4)2-1,2-C2B10H10 (R = H, p-Me). The solid-state structures of 9-RC6H4-1,2-C2B10H11 (R = p-NMe2, p-OCH2OMe, o-OMe, o-CN, p-CN, m-COOEt, and p-COOEt) and 9,12-(p-MeC6H4)2-1,2-C2B10H10 were determined by single crystal X-ray diffraction.

Download Full-text