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

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

1980 ◽  
Vol 33 (4) ◽  
pp. 853 ◽  
Author(s):  
HG Grant ◽  
PJ O'Regan ◽  
RJ Park ◽  
MD Sutherland

A common variety of Myoporum deserti A. Cunn. (Ellangowan Poison Bush) yields an essential oil consisting largely of the iridoid monoterpene, (1R)-1-methoxymyodesert-3-ene, C11H18O2,(1R,4aS,7R,7aR)-1-methoxy-4,7- dimethyl-1,4a,5,6,7,7a-hexahydrocycopenta[c]pyran, b.p. 67°/2 mm,[α]D- 165°. This cyclic acetal is hydrolysed to methanol and a mixture of two epimeric cyclopentanoid dialdehydes which are oxidized to the two epimeric trans,trans-nepetalinic acids and yield (+)-(R)-actinidine with Brady's reagent. (1R)-1-Methoxymyodesert-3-ene is oxidized by ozone/hydrogen peroxide to (1R,2R,5R)-2-acetyl-5- methylcyclopentanecarboxylic acid. Hydrogenation yields mainly (1R)- methoxymyodesertan, hydrolysed by aqueous maleic acid at room temperature to methanol and a cyclic hemiacetal, (1R,4R,4aR,7R,7aR)- 4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopenta[c]pyran-1-ol. Oxidation of this cis,cis-hemiacetal by bromine in acetate buffer yields a lactone further oxidized by chromic acid to (2R,1'S,2'R,3'R)- 2-(2'-carboxy-3'-methylcyclopentyl)-propionic acid.��� (1R)-1-Methoxymyodesertan, refluxed with aqueous phthalic acid, yields (+)-(4R,4aR,7R)-4,7-dimethyl-3,4,4a,5,6,7-hexahydrocyclopenta[c]pyran. Treatment of the hexahydropenta[c]pyran, the cis,cis-hemiacetal or (1R)-1-methoxymyodesertan with hydrochloric acid yields a trans,trans-hemiacetal, (1R,4R,4aR,7R,7aS)-4,7-dimethyl- 1,3,4,4a,5,6,7,7a-octahydrocyclopenta[c]pyran-1-ol, which equilibrates in solution to a mixture of α- and β-anomers. Spectral studies of these and otherproducts establish the configuration of the natural product at C1.��� (1R)-1-Methoxymyodesert-3-ene is not toxic to sheep as are the β- substituted furans characteristic of most other chemovarieties of M. deserti.


1958 ◽  
Vol 36 (3) ◽  
pp. 496-506 ◽  
Author(s):  
E. J. Tarlton ◽  
A. F. McKay

Glycine and β-alanine on condensation with carbon disulphide gave the corresponding l,3-di-(carboxyalkyl) thioureas. l,3-Di-(carboxymethyl) thiourea is rearranged to 2-thio-3-(carboxymethyl) hydantoin by warming with hydrochloric acid solution or heating above its melting point. Evidence is presented for the reversible condensation of 2 mole equivalents of the sodium salt of 2-thio-3-(carboxymethyl) hydantoin by the elimination of water. This condensation product is obtained as well-defined pink crystals. l,3-Di-(β-carboxyethyl) thiourea was oxidized with an alkaline solution of hydrogen peroxide or sodium hypochlorite solution to l,3-di-(β-carboxyethyl) urea. l,3-Di-(β-carboxyethyl) thiourea and l,3-di-(β-carboxyethyl) urea have been cyclized by heating with p-toluenesulphonic acid. The products were 2-thio-3-(β-carboxyethyI) hydrouracil and 3-(β-carboxyethyl) hydrouracil respectively.


1998 ◽  
Vol 76 (4) ◽  
pp. 469-476 ◽  
Author(s):  
M ZA Badr ◽  
A A Geies ◽  
M S Abbady ◽  
A A Dahy

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.


Author(s):  
Hingrajia Dhaval ◽  
Thanki Pragna ◽  
Modha Jayesh

Condensation of 2-hydrazinyl-1,6-dihydro-1-methyl-6-oxo-4-isobutylpyrimidine-5-carbonitrile (3) with different aromatic aldehyde gave the corresponding 2-(Benzylidinehydrazinyl)-1,6-dihydro-6-oxo-4-isobutylpyrimidine-5-carbonitrile (4). The reaction between 1,6-dihydro-1-methyl-2-(methylthio)-6-oxo-4-isobutylpyrimidine-5-carbonitrile (2) with hydrazine hydrate furnished (3). The condensation of 1,2,3,4-tetrahydro-4-oxo-6-isobutyl-2-thioxopyrimidine-5-carbonitrile (1) with methyl iodide yielded 2. Finally the products were characterized by 1H NMR, Mass and IR Spectra.


2015 ◽  
Vol 19 (0) ◽  
pp. 55-58
Author(s):  
Zhen-xue Liu ◽  
◽  
Zhong-xue Gan ◽  
Jun-jie Gu ◽  
Qing-feng Song

2020 ◽  
Vol 17 ◽  
Author(s):  
Ravi Bansal ◽  
Pradeep K. Soni ◽  
Neha Gupta ◽  
Sameer S. Bhagyawant ◽  
Anand K. Halve

Aims: In this article we have developed an eco-friendly one-pot multi-component reaction methodology was employed for the green synthesis of functionalized pyrazole derivatives viz cyclo-condensation of aromatic aldehydes, ethyl acetoacetate and phenyl hydrazine and/or hydrazine hydrate in the presence of cetyltrimethylammoniumbromide (CTAB) at 90°C temperature in aqueous medium. Method: In the present protocol we developed a green method for the synthesis of functionalized pyrazole derivatives through one-pot, multi-component cyclo-condensation of aromatic aldehydes, phenyl hydrazine or hydrazine hydrate and ethyl acetoacetate using cetyltrimethylammoniumbromide (CTAB) as a catalyst in water as solvent. Our methodology confers advantages such as short reaction time, atom economy, purification of product without using column chromatographic and hazardous solvent. The reaction is being catalyzed by cetyltrimethylammoniumbromide (CTAB) and thus products are formed under the green reaction conditions. Results: Initially the reaction of benzaldehyde and phenylhydrazine with ethyl acetoacetate was carried out in water at room temperature in the absence of the catalyst; no product was obtained after 24 h (Table 1 entry 1). When the reaction was carried out using L-proline as catalyst in ethanol at 70°C the yield of product was 20. Conclusion: This research not only provides a green and efficient method for the synthesis of sulfinic esters but also shows new applications of electrochemistry in organic synthesis. We consider that this green and efficient synthetic protocol used to prepare sulfinic esters will have good applications in future. In conclusion, we have developed successfully a green and efficient one-pot multi-component methodology for the synthesis of substituted pyrazoles using CTAB as a catalyst in water as solvent with excellent yields. Purifications of compounds were achieved without the use of traditional chromatographic procedures. This methodology has advantages of operational simplicity, clean reaction profiles and relatively broad scope which make it more attractive for the diversity oriented synthesis of these heterocyclic libraries. In this methodology we suggest the further alternative possibility for formation of substituted pyrazoles. The compound 7h can be used as an anticancer drug in pharma industry.


2021 ◽  
Author(s):  
Huiqi Wang ◽  
Duo An ◽  
Mei Wang ◽  
Liwen Sun ◽  
Ying Li ◽  
...  

Crystalline borophene quantum dots with two-photo fluorescence and their derivative boron nanospheres with hydrazine hydrate-dependent photoluminescence properties were prepared by efficient high-power sonication method combined with chemical exfoliation and one-step...


Holzforschung ◽  
2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Ajinkya More ◽  
Thomas Elder ◽  
Zhihua Jiang

Abstract This review discusses the main factors that govern the oxidation processes of lignins into aromatic aldehydes and acids using hydrogen peroxide. Aromatic aldehydes and acids are produced in the oxidative degradation of lignin whereas mono and dicarboxylic acids are the main products. The stability of hydrogen peroxide under the reaction conditions is an important factor that needs to be addressed for selectively improving the yield of aromatic aldehydes. Hydrogen peroxide in the presence of heavy metal ions readily decomposes, leading to minor degradation of lignin. This degradation results in quinones which are highly reactive towards peroxide. Under these reaction conditions, the pH of the reaction medium defines the reaction mechanism and the product distribution. Under acidic conditions, hydrogen peroxide reacts electrophilically with electron rich aromatic and olefinic structures at comparatively higher temperatures. In contrast, under alkaline conditions it reacts nucleophilically with electron deficient carbonyl and conjugated carbonyl structures in lignin. The reaction pattern in the oxidation of lignin usually involves cleavage of the aromatic ring, the aliphatic side chain or other linkages which will be discussed in this review.


2014 ◽  
Vol 2 (36) ◽  
pp. 7477-7481 ◽  
Author(s):  
Xinwei Dong ◽  
Yanjie Su ◽  
Huijuan Geng ◽  
Zhongli Li ◽  
Chao Yang ◽  
...  

N-doped CDs can be obtained directly with high yield by pyrolyzing ethanolamine in air within just 7 minutes with the assistance of hydrogen peroxide.


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