NEW PYRIMIDINE DERIVATIVES: SYNTHESIS AND APPLICATION OF THIAZOLO[3,2-a]-TRIAZOLO[4,3-a]-PYRIMIDINE AS BACTERICIDES, FUNGICIDES AND BIOREGULATORS

Khalil, Z. H.; Hafez, Ali A. Abdel; Ahmed, Ahmed Abdo

doi:10.1080/10426508908046079

Cited by 21 publications

(15 citation statements)

References 3 publications

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“…The deshielding of the o rth o p h e nyl p ro to n s in both derivatives by ab o u t 0.5 ppm relative to the m eta and p a ra proto n s indicated th at the phenyl group is coplanar with th e pyrim i dine ring leading to the conclusion th at N -l is u n substituted. O therw ise, the phenyl p ro to n s m ay give a com pact signals indicating th at th e phenyl group is tw isted out of plane of the pyrim idine nucleus because of the steric interaction resulting from the substituent at N -l. R eaction of the hydrazine 6 with form ic acid in eth an o l gave the formyl derivative 7 w hose ring closure gave th e triazole 8a [29]. A lternatively, the la tte r triazole can be obtain ed by heating of 6 with form ic acid.…”

Section: R*'mentioning

confidence: 99%

Synthesis and Dimroth Rearrangement of 6-Cyano-l,2,4-triazolo- [4,3-a]pyrimidin-5- and 7-ones. A Novel Alkylation with Orthoesters and a New Participation of the Cyano Group in the Rearrangement

Ashry¹,

Kilany²,

Rashed³

et al. 1998

Zeitschrift Für Naturforschung B

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The cyclization products of 5-cyano-2-hydrazino-6-phenyl-3,4-dihydropyrimidin-4-one (6) with one carbon inserting agents have been confirmed to be of the l,2,4-triazolo[4,3-a]pyrimidin-5(8//)-ones type and not the respective 7-ones, by comparing their alkylated deriva tives 10a, 11a, 27 and 28 with the product from the cyclization of the 3-methyl and 3-benzyl derivatives of 6. A novel alkylation process was found when triethyl orthoformate was used as a cyclizing agent. Dimroth rearrangement of 8, 14, 15, 24, 34 and 36 with 2% ethanolic KOH gave the respective triazolo[l,5-a]pyrimidinone 13, 18, 19, 25, 38 and 40, respectively. Using 10% ethanolic KOH led to a novel participation of the cyano group in the rearrange ment whereby 8a gave 7-imino-5-phenyl-l,2,4-triazolo[l,5-a]pyrimidine 22.

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Section: R*'mentioning

confidence: 99%

Synthesis and Dimroth Rearrangement of 6-Cyano-l,2,4-triazolo- [4,3-a]pyrimidin-5- and 7-ones. A Novel Alkylation with Orthoesters and a New Participation of the Cyano Group in the Rearrangement

Ashry¹,

Kilany²,

Rashed³

et al. 1998

Zeitschrift Für Naturforschung B

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“…5‐Cyano‐4‐oxo‐6‐phenyl‐2‐thioxo‐1,2,3,4‐tetrahydropyrimidine ( 1 ) has been synthesized via multicomponents reaction by one pot condensation reaction according to the reported procedure , was reacted with ethyl iodide and sodium acetate in refluxing ethanol gave 2‐ethylmercapto‐4‐oxo‐6‐phenyl‐pyrimidine‐5‐carbonitriles ( 2 ) according to the literature procedure . The ethylmercaptopyrim‐idinecarbonitriles derivative ( 2 ) was reacted with p ‐toluidine in ethanol under reflux to give 2‐( p ‐tolylamino)‐6‐oxo‐4‐phenyl‐1,6‐dihydropyrimidine‐5‐carbonitrile ( 3 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of New Fused Thienopyrimidines Derivatives as Anti‐inflammatory Agents

Tolba

Ahmed

El‐Dean

et al. 2017

Journal of Heterocyclic Chem

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5‐Amino‐2‐(p‐tolylamino)‐4‐phenylthieno[2,3‐d]pyrimidine‐6‐carbonitrile 9, which was synthesized by an innovative method, was used as a versatile precursor for synthesizing pyrimido‐thienopyrimidine, triazolopyrimidothienopyrimidine, and pyrimidothienotriazine compounds. Thus, reaction of aminothienopyrimidinecarbonitrile 9 with chloroacetylchloride in dioxane afforded the chloroacetylaminocarbonitrile derivative 10, which underwent nucleophilic substitution reactions with various primary and secondary amines gave the corresponding N‐alkyl‐(aryl)amino acetamides 11a,b. On the other hand, the reaction of aminocarbonitrile 9 with triethyl orthoformate followed by cyclization with hydrazine yielded an aminoiminopyrimidine derivative 13. The latter was used as versatile precursor for synthesis of new heterocyclic compounds. The structures of all the new compounds have been established on the basis of their analytical and spectral data (IR, 1H NMR, 13C NMR, and MS). Some of the synthesized compounds were evaluated in vitro for their anti‐inflammatory activity. All the tested compounds exhibited remarkable anti‐inflammatory activity.

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“…2-(Ethylthio)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitriles (2) synthesized from 1 according to a reported procedure, 33 when allowed to react with p-toluidine in ethanol under reflux gave 2-(p-tolylamino)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile (3) (Scheme 1). Chlorination of 3, by heating with an excess of phosphorus oxychloride, produced 4-chloro-2-(p-tolylamino)-6-phenyl-5-pyrimidinecarbonitrile (4) in good yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and antimicrobial activity of some new thienopyrimidine derivatives

Tolba¹,

El‐Dean²,

Ahmed³

et al. 2017

Arkivoc

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NEW PYRIMIDINE DERIVATIVES: SYNTHESIS AND APPLICATION OF THIAZOLO[3,2-a]-TRIAZOLO[4,3-a]-PYRIMIDINE AS BACTERICIDES, FUNGICIDES AND BIOREGULATORS

Cited by 21 publications

References 3 publications

Synthesis and Dimroth Rearrangement of 6-Cyano-l,2,4-triazolo- [4,3-a]pyrimidin-5- and 7-ones. A Novel Alkylation with Orthoesters and a New Participation of the Cyano Group in the Rearrangement

Synthesis and Dimroth Rearrangement of 6-Cyano-l,2,4-triazolo- [4,3-a]pyrimidin-5- and 7-ones. A Novel Alkylation with Orthoesters and a New Participation of the Cyano Group in the Rearrangement

Synthesis of New Fused Thienopyrimidines Derivatives as Anti‐inflammatory Agents

Synthesis and antimicrobial activity of some new thienopyrimidine derivatives

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