New heterocycles from thienopyridocinnolines

1998 ◽  
Vol 76 (4) ◽  
pp. 469-476 ◽  
Author(s):  
M ZA Badr ◽  
A A Geies ◽  
M S Abbady ◽  
A A Dahy
Keyword(s):  
Acetic Anhydride ◽  
Hydrazine Hydrate ◽  
Nitrous Acid ◽  
Ammonium Acetate ◽  
Carbon Disulphide ◽  
Sodium Ethoxide ◽  
Ring Closure ◽  
Ethyl Chloroformate ◽  
Intramolecular Ring

3-Cyano-4-(p-tolyl)pyrido[3,2-c]cinnolin-2(1H) thione 3 was reacted with α -halo ketones, esters, or amides to give the intermediates, S-alkylated products 5b-h, respectively, which underwent intramolecular ring closure reactions with ethanolic sodium ethoxide to give thienopyridocinnolines 6a-h. Pyrimidothienopyridocinnolines 9 and 11 were obtained by treatment of oxazino compound 8 with hydrazine hydrate and ammonium acetate. Treatment of hydrazino derivative 13 with acetylacetone, triethylorthoformate, carbon disulphide, ethyl chloroformate, and acetic anhydride afforded triazolopyrimidothienopyridocinnolines 14-16, 18, and 21, while with nitrous acid the corresponding tetrazolo compound 19 was produced.Key words: thienopyridocinnolines; their pyrimido, triazolopyrimido, and heteroannelated systems.

scholarly journals Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives

1999 ◽  
Vol 64 (11) ◽  
pp. 655-662 ◽  
Author(s):  
Samira Swelam ◽  
Abd El-Salam ◽  
Magdi Zaki
Keyword(s):  
Acetic Anhydride ◽  
Formic Acid ◽  
Hydrazine Hydrate ◽  
Carbon Disulfide ◽  
Nitrous Acid ◽  
Reaction Medium ◽  
Pyrimidine Derivatives ◽  
Elemental Analyses ◽  
Tetrazole Derivatives

Reaction of 2 with different reagents, namely formic acid, acetic anhydride and trichloroacetonitrile, yielded pyrazolo[3,4-d]pyrimidine derivatives 3, 5 and 6, respectively. Pyrazolo[3,4-d]pyrimidine m-thiazine(7) and 2,4-(1H,3H)dithione (8) derivatives were formed by the action of carbon disulfide on 2, depending on the reaction medium. Interaction of 7 with hydrazine hydrate yielded the aminoimino derivative 9 which reacted with acetic anhydride, triethyl orthoacetate and/or appropriate aldehydes to give 11, 12 and 13a,b, respectively. Methylation of compound 8 gave 14, which reacted with hydrazine hydrate to afford the monohydrazino derivative 15. Reaction of 15, with formic acid and nitrous acid afforded pyrazolo[4,3-e]triazolo[1,5-c]pyrimidine (16) and pyrazolo[4,3-e]tetrazolo-[1,5-c]pyrimidine (17) derivatives, respectively. The structures of products 3-17 were identified in light of their elemental analyses and spectra data.

A One Step Synthesis of New 4-Aminopyrimidine Derivatives: Preparation of Tetrazolo- and s-Triazolopyrimidines

1983 ◽  
Vol 38 (12) ◽  
pp. 1686-1689 ◽  
Author(s):  
Hamed A. Daboun ◽  
Ahmed M. El-Reedy
Keyword(s):  
Hydrogen Peroxide ◽  
Hydrochloric Acid ◽  
Hydrazine Hydrate ◽  
Aromatic Aldehyde ◽  
Methyl Iodide ◽  
Nitrous Acid ◽  
Carbon Disulphide ◽  
Aromatic Aldehydes ◽  
Spectral Studies ◽  
One Step

2-Mercapto-4-amino-5-cyano-6-arylpyrimidines (1a, b), 2-hydroxy derivatives 1c, d and 2-methylmercapto derivatives 4 a, b were synthesised via the reaction of either a mixture of malononitrile and aromatic aldehyde or arylidene malononitrile with thiourea, urea and S-methylisothiourea, respectively. 1c, d could also be obtained by the action of hydrogen peroxide on 1a, b or by the action of hydrochloric acid on 4a, b. Compounds 4a, b could also be prepared by the action of methyl iodide on 1a, b. 4a reacted with hydrazine hydrate to give the 2-hydrazino derivative 5 which condensed easily with aromatic aldehydes to give the Schiff’s bases 6 a, b. Compound 5 could be converted into the tetrazolo-and s-triazolopyrimidines 7 and 9 by the action of nitrous acid and carbon disulphide respectively. Structures of the newly synthesised compounds were established by chemical routes and spectral studies

Synthesis of Schiff’s Bases of 1,2,4-Triazole Derivatives under Microwave Irradiation Technique and Evaluation of Their Anti-diabetic Activity

2021 ◽  
Vol 08 ◽  
Author(s):  
Krishna Chandra Panda ◽  
B.V.V Ravi Kumar ◽  
Biswa Mohan Sahoo
Keyword(s):  
Hydrazine Hydrate ◽  
Carbon Disulphide ◽  
Potassium Hydroxide Solution ◽  
Ring Closure ◽  
Biologically Active ◽  
Schiff’S Bases ◽  
Standard Drug ◽  
Triazole Derivatives ◽  
Schiff's Bases

Background: Schiff bases play key role for the generation of a large number of biologically active compounds via cycloaddition, replacement and ring closure reactions. Objective: The objective of this study is to optimize the purity and yield of product, reaction time, eco-friendly reaction by the help of microwave assisted organic synthesis. Methods: New series of Schiff’s bases of triazole derivatives were achieved via multicomponent reactions. The starting material benzohydrazide 1 was obtained by esterification of bezoyl chloride with methanol in presence of concentrated sulphuric acid followed by the reaction with hydrazine hydrate. Benzohydrazide was allowed to react with carbon disulphide in ethanolic potassium hydroxide solution to yield potassium dithiocarbazinate 2 which undergoes cyclization by reacting with hydrazine hydrate to afford 4-[amino]-5-phenyl-4H-1,2,4-triazole-3-thiol (3). Further, various Schiff’s bases 4a-f were obtained by reacting 1,2,4-triazole-3-thiol with different substituted benzaldehydes under microwave irradiations as a green and eco-friendly energy source. Results: The structures of the newly synthesized compounds were elucidated in accordance with their spectral data and elemental analysis. Conclusion : The obtained compounds exhibited significant in-vivo anti-diabetic activity as compared to the standard drug Metformin. The anti-diabetic effect was investigated by using Alloxan-induced diabetic model.

Synthesis of Pyrimidine, Thiazolopyrimidine, Pyrimidotriazine and Triazolopyrimidine Derivatives and their Biological Evaluation

1999 ◽  
Vol 54 (6) ◽  
pp. 788-798 ◽  
Author(s):  
Fawzy A. Attaby ◽  
Sanaa M. Eldin
Keyword(s):  
Biological Activity ◽  
Acetic Anhydride ◽  
Formic Acid ◽  
Hydrazine Hydrate ◽  
Carbon Disulfide ◽  
Biological Evaluation ◽  
The Other ◽  
Ethyl Chloroformate ◽  
Heterocyclic Derivatives ◽  
Active Methylene

Pyrimidin-4-one-2-thione (3) was synthesized via the reaction of thiourea (1) with ethyl benzoylacetate (2) and was taken as a starting material for the present study via its reactions with the halogen-containing reagents 6a-d and lOa-c to give the corresponding thiazolopyrimidines 8, 9 and 12a-c. The 2-hydrazino derivatives 5 were synthesized either via the reaction of 3 or 4 with hydrazine hydrate. Compound 5 reacted with 6a-c and lOa-c to give the corresponding pyrimidotriazines 17a-c and 19 respectively. Also, compound 5 reacted with the active methylene-containing reagents 13 and 2a,b to give the corresponding 2-pyrazolopyrimidines 15 and 22a,b respectively. On the other hand, the triazolopyrimidines 21a,b and 30a,b were also obtained via the reaction of 5 with each of formic acid, acetic anhydride, ethyl chloroformate and carbon disulfide respectively. Some of the newly synthesized heterocyclic derivatives were tested for their biological activity

scholarly journals TfOH-Promoted Reaction of 2,4-Diaryl-1,1,1-Trifluorobut-3-yn-2-oles with Arenes: Synthesis of 1,3-Diaryl-1-CF3-Indenes and Versatility of the Reaction Mechanisms

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3079 ◽  
Author(s):  
Aleksey V. Zerov ◽  
Anna N. Kazakova ◽  
Irina A. Boyarskaya ◽  
Taras L. Panikorovskii ◽  
Vitalii V. Suslonov ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Reaction Mechanisms ◽  
Room Temperature ◽  
Ring Closure ◽  
Nucleophilic Attack ◽  
New Process ◽  
Intramolecular Ring ◽  
Propargyl Alcohols

The TfOH-mediated reactions of 2,4-diaryl-1,1,1-trifluorobut-3-yn-2-oles (CF3-substituted diaryl propargyl alcohols) with arenes in CH2Cl2 afford 1,3-diaryl-1-CF3-indenes in yields up to 84%. This new process for synthesis of such CF3-indenes is complete at room temperature within one hour. The synthetic potential, scope, and limitations of this reaction were illustrated by more than 70 examples. The proposed reaction mechanism invokes the formation of highly reactive CF3-propargyl cation intermediates that can be trapped at the two mesomeric positions by the intermolecular nucleophilic attack of an arene partner with a subsequent intramolecular ring closure.

Carbonyl-Containing Spirodihydrofurans in Reactions with Ammonium Acetate and Hydrazine Hydrate.

ChemInform ◽  
2006 ◽  
Vol 37 (32) ◽  
Author(s):  
O. V. Fedotova ◽  
M. I. Skuratova ◽  
P. V. Reshetov ◽  
M. A. Panov
Keyword(s):  
Hydrazine Hydrate ◽  
Ammonium Acetate
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