Synthesis and heterocyclization of dithiocarbamoylacetoacetic esters and anilides

Dovlatyan, V. V.; Eliazyan, K. A.; Pivazyan, V. A.; Ghazaryan, Emma A.; Engoyan, A. P.; Grigoryan, Ruzanna; Mirzoyan, R. G.

doi:10.1007/bf02290851

Cited by 10 publications

(7 citation statements)

References 2 publications

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“…Three different procedures (A–C) have been applied in the Hantzsch reaction. The first one (A) consider the conventional Hantzsch reaction [1, 4, 5, 31–45], by refluxing an ethanol solution of 4 with thioamides, thiourea, and diphenylthiocarbazone for 4–6 h, being the reaction products obtained in good yields and without need of purification. Microwave irradiation was used as an alternative source of heating in the other methods, using ethanol as solvent (B) or in the solvent‐free reaction conditions (C).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and reactivity of 6‐methyl‐4H‐furo[3,2c]pyran‐3,4‐dione

Hikem-Oukacha

Rachedi

Hamdi

et al. 2010

Journal of Heterocyclic Chem

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An efficient synthesis of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one by bromination of dehydroacetic acid in glacial acetic acid is described. Novel 4‐hydroxy‐6‐methyl‐3‐(2‐substituted‐thiazol‐4‐yl)‐2H‐pyran‐2‐ones have been prepared from the reaction of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one with thioamides, thiourea, and diphenylthiocarbazone. The condensation reaction of 6‐methyl‐4H‐furo[3,2c]pyran‐3,4‐dione, obtained from the reaction of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one with aliphatic amines, with benzaldehydes and acetophenones led to novel 2‐arylidene‐6‐methyl‐2H‐furo[3,2‐c]pyran‐3,4‐diones and 6‐(2‐arylprop‐1‐enyl)‐2H‐furo[3,2‐c]pyran‐3,4‐diones. The structure of all compounds was established by elemental analysis, IR, NMR, and mass spectra. J. Heterocyclic Chem., 2011.

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Section: Resultsmentioning

confidence: 99%

Synthesis and reactivity of 6‐methyl‐4H‐furo[3,2c]pyran‐3,4‐dione

Hikem-Oukacha

Rachedi

Hamdi

et al. 2010

Journal of Heterocyclic Chem

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“…The condensation reaction of B-diketones or B-ketocarboxylic esters with arylsulfonyl guanidine is a well-known reaction for the preparation of sulfapyrimidine derivatives [19][20][21]. Another approach for the synthesis of sulfapyrimidine derivatives is by reacting different 2-aminopyrimidines to arylsulfonyl chloride [22]. Several derivatives of diphenysulfapyrimidine acetates have also been synthesized by reacting chalcones with sulfaguanidine acetate [23,24].…”

Section: Introductionmentioning

confidence: 99%

Tailored‐design Synthesis of Sulfapyrimidine Derivatives

Azzam

2018

Journal of Heterocyclic Chem

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In this paper, we report an efficient and convenient approach for the synthesis of tailored‐design target sulfapyrimidine derivatives expected to show remarkable antimicrobial activities. The approach is based on reacting arylsulfonyl guanidine with α,β‐unsaturated carbonyl compounds to afford N‐(4,6‐diarylpyrimidin‐2‐yl)arylsulfonamide or with ylidene derivatives to afford N‐(6‐aryl‐5‐cyanopyrimidin‐2‐yl)arylsulfonamide, N‐(4‐amino‐5‐cyano‐6‐(methylthio)‐pyrimidin‐2‐yl)‐arylsulfonamide, and N‐(5‐cyanopyrimidin‐2‐yl)arylsulfonamide compounds through Michael addition reaction. The structure of the newly synthesized compounds was confirmed from spectral data and elemental analysis.

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“…10 Due to the significance of thiazole derivatives in medicinal chemistry, considerable effort has been devoted to develop alternate routes for their synthesis. [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] Although several strategies with variable yields have been reported for the synthesis of steroidal as well as non-steroidal thiazoles, the Hantzsch's protocol [29][30][31] continues to be a method of choice involving the reaction of α-halocarbonyl compound with an appropriate thiourea or thioamide. Thus, we have also selected the Hantzsch's protocol for this purpose, 5-bromosteroidal ketones, [32][33] are selected instead of 7-bromosteroidal ketones because both lead to the same product but preparation of 7-bromocholestan-6-one [20][21] is much more tedious leading to a mixture of products.…”

Section: Introductionmentioning

confidence: 99%

A Facile Synthesis of 6,7-Fused Steroidal Thiazoles via 1,3-Intramolecular Migration of Bromine/Allylic Displacement of Bromine

Alam¹,

Khan

2008

J. Chil. Chem. Soc.

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A facile synthesis of an array of 6,7-fused steroidal thiazoles (4-9) is reported. Replacement of lachrymatory 7-bromosteroidal ketones (4a) with readily accessible 5-bromosteroidal ketones (1-3), as a starting material, on simple condensation with thiourea or phenylthiourea gives the thiazole fused ring products. The products have been characterized on the basis of microanalytical and spectral data, which find support in some cases from comparison with previously known samples. A rationalization for the routes of conversion is given, based on current and previous results.

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Synthesis and heterocyclization of dithiocarbamoylacetoacetic esters and anilides

Abstract: The action o [" salt.; of N-monosubstituted ['4-methyl-3-methyl(ao,l)-2-thiooxy-l,3-thiazolyl-5-carboxylic acids, which can be converted to the corresponding acid, acid chloride, and anilide.

Cited by 10 publications

References 2 publications

Synthesis and reactivity of 6‐methyl‐4H‐furo[3,2c]pyran‐3,4‐dione

Synthesis and reactivity of 6‐methyl‐4H‐furo[3,2c]pyran‐3,4‐dione

Tailored‐design Synthesis of Sulfapyrimidine Derivatives

A Facile Synthesis of 6,7-Fused Steroidal Thiazoles via 1,3-Intramolecular Migration of Bromine/Allylic Displacement of Bromine

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