Journal ArticleDOI
Chemistry of Substituted Quinolines: Thieno[2,3- b ] and Thiopyrano[2,3- b ]quinolines
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TLDR
In this paper, a mixture of 3-formyl-2-chloroquinolines with thioglycolic acid was obtained in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2 carboxylic acids in a 30-40% yield.Abstract:
The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60–70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30–40% yield, respectively. The uncyclized compounds on refluxing with POCl 3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, 1 H NMR, and mass spectral data.read more
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Journal ArticleDOI
Recent advances in the chemistry of thieno[2,3-b]pyridines 1. Methods of synthesis of thieno[2,3-b]pyridines
TL;DR: The recent data (2007-2018) on the synthesis of thieno[2,3-b]pyridines are summarized and systematized in this paper.
Journal ArticleDOI
A glycerol mediated domino reaction: an efficient, green synthesis of polyheterocycles incorporating a new thiochromeno[2,3-b]quinoline unit
TL;DR: One-pot synthesis of polyheterocycles, all of which incorporate a new thiochromeno[2,3-b]quinoline unit, has been demonstrated via a domino/Knoevenagel-hetero-Diels-Alder (DKHDA) reaction.
Journal ArticleDOI
Facile “on water” domino reactions for the expedient synthesis of 2H-thiopyrano[2,3-b]quinolines
TL;DR: In this article, a facile synthesis of novel 3-nitro-2-aryl-2H-thiopyrano[2,3-b]quinolines from the domino reactions of 2-mercaptoquinoline-3-carbaldehyde and substituted β-nitrostyrenes in the presence of triethylamine (TEA) in water is described.
Journal ArticleDOI
An efficient domino Knoevenagel/hetero-Diels–Alder route to some novel thiochromenoquinoline-fused polyheterocycles
TL;DR: The 2-alkenylthiopyranoquinoline-3-carbaldehyde derived from 2-mercaptoquinoline, 3-caraldehyde and citral as mentioned in this paper underwent smooth domino Knoevenagel/hetero-Diels-Alder reaction with heterocyclic mono- or diketones in tetrabutylammonium hydrogensulfate under solvent-free conditions and afforded a new class of thiochromenoquinoline fused heterocycles in good yields.
Journal ArticleDOI
Design, synthesis, and in silico studies of quinoline-based-benzo[d]imidazole bearing different acetamide derivatives as potent α-glucosidase inhibitors
Milad Noori,Ali Davoodi,Aida Iraji,Navid Dastyafteh,Minoo Khalili,Mehdi Asadi,Maryam Mohammadi Khanaposhtani,Somayeh Mojtabavi,Mehdi Dianatpour,Mohammad Ali Faramarzi,Bagher Larijani,Massoud Amanlou,Mohammad Mahdavi +12 more
TL;DR: In this article , 18 quinoline-based-benzo[d]imidazole derivatives were synthesized and screened for their α-glucosidase inhibitory potential.
References
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Book
Comprehensive Heterocyclic Chemistry II
TL;DR: In this article, the CHEC III is organized in 15 volumes and closely follows the organization used in the previous edition: Volumes 1 and 2: Cover respectively three and four-membered heterocycles, together with all fused systems containing a three- or four-measured heterocyclic ring.
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A versatile new synthesis of quinolines and related fused pyridines, Part 5. The synthesis of 2-chloroquinoline-3-carbaldehydes
TL;DR: In this article, Vilsmeier's reagent was used to convert 2-chloroquinoline-3-carbaldehydes in good yield by the action of the reagent in a phosphoryl chloride solution.
Journal ArticleDOI
A versatile new synthesis of quinolines and related fused pyridines. Part 9. Synthetic application of the 2-chloroquinoline-3-carbaldehydes
Otto Meth-Cohn,Bramha Narine,Brian Tarnowski,Roy Hayes,Amitis Keyzad,Salah Rhouati,Andrew J. Robinson +6 more
TL;DR: The 2-chloro-groups of the title compounds have been replaced by H, I, OH, SR, Li, CO2H, CHO, Ph, piperidine, and N3 giving a tetrazole.
Journal ArticleDOI
Structure--activity relationships in a series of novel 3,4-dihydro-4-oxopyrimido[4,5-b]quinoline-2-carboxylic acid antiallergy agents.
TL;DR: Structural--activity data suggest that the presence of a carboxylic acid moiety at the 2 position affords optimal potency and that esters are preferred for good oral absorption.