Efficient Regioselective Synthesis of Novel Condensed Sulfur–Nitrogen Heterocyclic Compounds Based on Annulation Reactions of 2-Quinolinesulfenyl Halides with Alkenes and Cycloalkenes

The preparation of novel reagents 2-quinolinesulfenyl chloride and bromide based on available 2-mercaptoquinoline has been described. This approach opens up opportunities for the introduction of 2-quinolinesulfenyl chloride and bromide into organic synthesis. Regioselective synthesis of novel 1,2-dihydro[1,3]thiazolo[3,2-a]quinolin-10-ium derivatives in high yields has been developed by annulation reactions of 2-quinolinesulfenyl chloride and bromide with alkenes. Condensed tetracyclic products have been obtained by the reactions of 2-quinolinesulfenyl chloride and bromide with cycloalkenes. The opposite regiochemistry in the reactions with styrene, isoeugenol and 1-alkenes was discussed.

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Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent

Chemical Papers ◽

10.2478/s11696-011-0018-1 ◽

2011 ◽

Vol 65 (3) ◽

Cited By ~ 3

Author(s):

Selvaraj Roopan ◽

Fazlur-Rahman Khan ◽

Jong Jin

Keyword(s):

Natural Product ◽

Organic Synthesis ◽

Heterocyclic Compounds ◽

Building Blocks ◽

Natural Product Synthesis ◽

Mitsunobu Reaction ◽

Reaction Conditions ◽

Diethyl Azodicarboxylate ◽

Nitrogen Heterocyclic

AbstractThe Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

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OnePot Regioselective Synthesis of Heterocyclic Compounds by the Application of Sonogashira Reaction as One of the Steps: A Review

Journal of Chemistry and Chemical Sciences ◽

10.29055/jccs/576 ◽

2018 ◽

Vol 8 (2) ◽

pp. 212-230

Author(s):

Sanjay Nath

Keyword(s):

Heterocyclic Compounds ◽

Regioselective Synthesis ◽

Sonogashira Reaction ◽

One Pot

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Ionic Liquids for the Synthesis of Five-Membered N,N-, N,N,N- and N,N,N,NHeterocycles

Current Organic Chemistry ◽

10.2174/1385272823666190717101741 ◽

2019 ◽

Vol 23 (11) ◽

pp. 1214-1238 ◽

Cited By ~ 3

Author(s):

Navjeet Kaur ◽

Pranshu Bhardwaj ◽

Meenu Devi ◽

Yamini Verma ◽

Neha Ahlawat ◽

...

Keyword(s):

Ionic Liquids ◽

Organic Synthesis ◽

Heterocyclic Compounds ◽

Reaction Medium ◽

Environmental Issues ◽

Organic Reaction ◽

Environment Friendly ◽

The Past ◽

Area Of Interest ◽

Major Subject

Due to special properties of ILs (Ionic Liquids) like their wide liquid range, good solvating ability, negligible vapour pressure, non-inflammability, environment friendly medium, high thermal stability, easy recycling and rate promoters etc. they are used in organic synthesis. The investigation for the replacement of organic solvents in organic synthesis is a growing area of interest due to increasing environmental issues. Therefore, ionic liquids have attracted the attention of chemists and act as a catalyst and reaction medium in organic reaction with high activity. There is no doubt that ionic liquids have become a major subject of study for modern chemistry. In comparison to traditional processes the use of ionic liquids resulted in improved, complimentary or alternative selectivities in organic synthesis. The present manuscript reported the synthesis of multiple nitrogen containing five-membered heterocyclic compounds using ionic liquids. This review covered interesting discoveries in the past few years.

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Polar Diels-Alder Reactions Under Microwave Irradiation Employing Different Heterocyclic Compounds as Electrophiles

Mini-Reviews in Organic Chemistry ◽

10.2174/1570193x15666180608083925 ◽

2019 ◽

Vol 16 (6) ◽

pp. 527-543 ◽

Cited By ~ 1

Author(s):

Pedro M.E. Mancini ◽

Carla M. Ormachea ◽

María N. Kneeteman

Keyword(s):

Organic Synthesis ◽

Heterocyclic Compounds ◽

Ionic Conduction ◽

Theoretical Calculations ◽

Cycloaddition Reaction ◽

Diels Alder ◽

The Other ◽

Conventional Heating ◽

Protic Ionic Liquids ◽

Solvent Free Conditions

During the last twenty years, our research group has been working with aromatic nitrosubstituted compounds acting as electrophiles in Polar Diels-Alder (P-DA) reactions with different dienes of diverse nucleophilicity. In this type of reaction, after the cycloaddition reaction, the nitrated compounds obtained as the [4+2] cycloadducts suffer cis-extrusion with the loss of nitrous acid and a subsequent aromatization. In this form, the reaction results are irreversible. On the other hand, the microwave-assisted controlled heating become a powerful tool in organic synthesis as it makes the reaction mixture undergo heating by a combination of thermal effects, dipolar polarization and ionic conduction. As the Diels-Alder (D-A) reaction is one of the most important process in organic synthesis, the microwave (MW) irradiation was applied instead of conventional heating, and this resulted in better yields and shorter reaction times. Several substituted heterocyclic compounds were used as electrophiles and different dienes as nucleophiles. Two experimental situations are involved: one in the presence of Protic Ionic Liquids (PILs) as solvent and the other under solvent-free conditions. The analysis is based on experimental data and theoretical calculations.

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UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽

10.1055/a-1736-4388 ◽

2022 ◽

Author(s):

Dishu Zeng ◽

Tianbao Yang ◽

Niu Tang ◽

Wei Deng ◽

Jiannan Xiang ◽

...

Keyword(s):

Amino Acid ◽

Organic Synthesis ◽

Efficient Method ◽

Building Block ◽

Room Temperature ◽

Uv Light ◽

Amino Acid Derivatives ◽

One Pot ◽

Plausible Mechanism ◽

High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

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Pd-catalysed general access to 7-membered N/O-heterocyclic compounds as potential agents against inflammation

Chemical Communications ◽

10.1039/d1cc04140a ◽

2021 ◽

Vol 57 (78) ◽

pp. 10091-10094

Author(s):

B. Thirupataiah ◽

Gangireddy Sujeevan Reddy ◽

Guntipally Mounika ◽

Jetta Sandeep Kumar ◽

Kazi Amirul Hossain ◽

...

Keyword(s):

Heterocyclic Compounds ◽

Bond Formation ◽

Regioselective Synthesis

A Pd-catalysed regioselective synthesis of 4,5-disubstituted 7-membered N/O-heterocycles was achieved via the 7-endo-dig cyclization followed by C–C bond formation of 2-(1-alkynyl)phenylacetamide.

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