Reactions with acetoacetanilide: Synthesis and antibacterial activity of some new pyran, pyrano[2,3-c]pyrazole and pyrano[2,3-c]-pyridine derivatives

Riad, Bahia Y.; Abdelhamid, Abdou O.; Khalifa, F. A.; Saleh, Y. E.

doi:10.1007/bf02855555

Cited by 10 publications

(9 citation statements)

References 11 publications

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“…The IR spectrum of compound 2 showed absorption bands assignable to the NH groups, CN-, and CO group. Its 1 H-NMR spectrum showed signals at 1.77 (s, 3H, C 3 -CH 3 ), 2.24 (s, 3H, O=C-CH 3 The structure of the aforementioned compound was confirmed by spectral data (see Experimental and Scheme 1). The 1 H-NMR spectrum showed a signal at 2.26 (s, 3H, C 3 -CH 3 ).…”

Section: Resultsmentioning

confidence: 55%

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Synthesis of Pyrazolo[4′,3′:5,6]pyrano[2,3‐d]pyrimidine Derivatives for Antiviral Evaluation

Shamroukh

Zaki

Morsy

et al. 2007

Archiv der Pharmazie

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6-Amino-3-methyl-4-(4-nitrophenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (1) was used as a precursor for preparation of some novel 3,7-dimethyl-4-(4-nitrophenyl)-2,4-dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidine derivatives 3-6, and some of their corresponding N(2)- and C(5)-S-acyclic nucleosides 7 and 8. Furthermore, the preparation of 5-amino-1-[3,7-dimethyl-4-(4-nitrophenyl)-2,4-dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidin-5-yl]-1H-pyrazole derivatives 10-16 were described. Some of the prepared products were selected and tested for antiviral activity against Herpes Simplex Virus type-1 (HSV-1).

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Section: Resultsmentioning

confidence: 55%

“…Pyrano [2,3-c]pyrazole derivatives showed biological activities as bactericides [3] and virucides [4]. Moreover, a large number of fused pyrimidine derivatives exhibited antimycobacterial [5], antitumor [6], and antiviral activities [7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyrazolo[4′,3′:5,6]pyrano[2,3‐d]pyrimidine Derivatives for Antiviral Evaluation

Shamroukh

Zaki

Morsy

et al. 2007

Archiv der Pharmazie

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“…28) (Scheme 51) or cyclized under acidic conditions gave pyran derivatives. 59 It was also observed that these pyranopyrazoles could be converted easily to pyrazolopyridines in acetic acid and ammonium acetete. These compounds showed moderate inhibition effect on bacteria.…”

Section: Figurementioning

confidence: 99%

“…58 Derivatives of compounds 28 showed moderate inhibition effect on bacteria. 59 Various derivatives of pyranopyrazoles 175-177 showed antibacterial, anti-inflammatory and cytotoxicity. 64 Pyrano[2,3-c]pyrazoles 192, 193 exhibited moderate antibacterial activity.…”

Section: Biological Activitiesmentioning

confidence: 99%

4H-Pyrano[2,3-c]pyrazoles: a review

Aslam¹,

White²,

Zafar³

et al. 2018

Arkivoc

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This review summarizes the synthetic pathways to pyrano [2,3-c]pyrazoles which either have a hydrogen atom, aryl substituent or condensed spiro group at the 4-position. Synthesis focuses on two component or MCR's including three, four and five components. Reaction conditions are variable including a green approach, nanoparticulate catalyst, microwave irradiation, ultrasonic irradiations and other catalysts. Most commonly used reagents are pyrazolones, benzylidenemalononitrile, hydrazines, β-ketoesters, malononitrile, aldehydes and ketones. Various substituted phenyl, naphthalene, anthracene, furan, thiophene, indole, tetrahydroquinoline have been incorporated at 4-position while amino and cyano groups at sixth and fifth position respectively and posses diverse biological properties.

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“…In particular, they play key role as intermediates in the synthesis of pyridines and pyrimidines (Dyachenko, 2005;Habashi et al, 1986;Lebed et al, 2012;Kumar et al, 2009;Riad et al, 1989;Sadek et al, 2011;Viale et al, 2011;Yadav et al, 2003;Yadav et al, 2011). They are prepared by the two component reaction of alkyl acetoacetate and different aromatic /hetero aromatic amines (Desai et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

Process optimization and eco-friendly/greener synthesis of some n-aryl/heteryl acetoacetamides

Sirisha¹,

Rajyalaxmi²,

Olivia³

2013

Int Curr Pharm J

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N-aryl/heteryl acetoacetamides are the intermediates used in the synthesis of various heterocyclic compounds like 1,4-dihydropyridines, pyrimidines etc. Three different substituted N-aryl/heteryl acetoacetamide derivatives (I-III) have been prepared from the reaction of ethylacetoacetate and three different aryl/heteryl primary amines under solvent free conditions using potassium tert-butoxide as catalyst. The reactions were carried out by two different methods (viz., Conventional and Microwave irradiation) and they are simple, eco-friendly and economical. All reactions were processed for optimization with different ratios of aryl/heteryl amine and ethylacetoacetate like1:1,1:1.2,1:1.4,1:1.6,1:1.8,1:2 and a comparison was made between the percentage yields with each ratio. Highest percentage yield was observed with 1:1.8 ratio for I & II and 1:1.6 ratio for III in both the methods. However, the microwave irradiation method was found to be superior to the conventional method. The newly synthesized compounds have been purified by recrystallization and characterized by physical and spectral data.DOI: http://dx.doi.org/10.3329/icpj.v2i11.16533 International Current Pharmaceutical Journal, October 2013, 2(11): 189-192

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Reactions with acetoacetanilide: Synthesis and antibacterial activity of some new pyran, pyrano[2,3-c]pyrazole and pyrano[2,3-c]-pyridine derivatives

Cited by 10 publications

References 11 publications

Synthesis of Pyrazolo[4′,3′:5,6]pyrano[2,3‐d]pyrimidine Derivatives for Antiviral Evaluation

Synthesis of Pyrazolo[4′,3′:5,6]pyrano[2,3‐d]pyrimidine Derivatives for Antiviral Evaluation

4H-Pyrano[2,3-c]pyrazoles: a review

Process optimization and eco-friendly/greener synthesis of some n-aryl/heteryl acetoacetamides

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