One‐pot PTC synthesis of polyfused pyrazoles

El-Saraf, G. A.; El-Sayed, A. M. A.; El‐Saghier, Ahmed M. M.

doi:10.1002/hc.10129

Cited by 20 publications

(9 citation statements)

References 16 publications

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“…Additionally, pyrazolones have been reported to be the key starting materials for the synthesis of commercial aryl/heteroaropyrazolone dyes (Basaif et al, 2007;Ho, 2005). Halogenated pyrazolones are also useful synthetic intermediates for synthesis of diazo-dyes (Kirschke et al, 1984), fused (Chande et al, 1993) and spiroheterocyclic compounds (El-Saraf & El-Sayed 2003). In this context we report the synthesis and crystal structure of the title compound.…”

Section: S1 Commentmentioning

confidence: 95%

“…For the diverse biological activities of pyrazolone compounds, see: Guckian et al (2010); Fan et al (2006); Castagnolo et al (2008); Idrees et al (2009); Abdel-Aziz et al (2009); Manojkumar et al (2009); Shete et al (2011); Sujatha et al (2009); El-Hawash et al (2006); Kawai et al (1997); Wu et al (20026). For industrial applications of pyrazolones, see: Basaif et al (2007); Ho (2005); Kirschke et al (1984); Chande et al (1993); El-Saraf & El-Sayed (2003). For graph-set motif notation, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

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3-Oxo-N′,2-diphenyl-2,3-dihydro-1H-pyrazole-4-carbohydrazide

et al. 2014

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In the title compound, C16H14N4O2, the pyrazole ring makes a dihedral angle of 10.49 (8)° with its N-bound phenyl group, while it is nearly perpendicular to the other phenyl ring [dihedral angle = 88.47 (5)°]. The molecular conformation is stabilized by intramolecular C—H⋯O and N—H⋯O hydrogen bonds. In the crystal, the packing involves sheets of molecules parallel to (100) linked by N—H⋯O hydrogen bonds. A C—H⋯O interaction is also observed.

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Section: S1 Commentmentioning

confidence: 95%

Section: Related Literaturementioning

confidence: 99%

3-Oxo-N′,2-diphenyl-2,3-dihydro-1H-pyrazole-4-carbohydrazide

et al. 2014

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“…Treatment of 3-amino-1-phenyl-2-pyrazoline-5-one 138 with CS 2 along with chloroacetonitrile, ethyl chloroacetate, or phenacyl bromide in 1 : 1 : 1 and 1 : 1 : 2 molar ratios using [dioxan/K 2 CO 3 /TBAB] as a PTC gave the corresponding thienopyrazoles 139-143, 145 and respectively, 144, 146 and 147, fused thiazines [52] (Figure 54).…”

Section: Synthesis Of Fused Five-membered Ring Heterocyclesmentioning

confidence: 99%

Synthesis and Reactions of Five-Membered Heterocycles Using Phase Transfer Catalyst (PTC) Techniques

El-Sayed

Allah

El‐Saghier

et al. 2014

Journal of Chemistry

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Phase transfer catalysts (PTCs) have been widely used for the synthesis of organic compounds particularly in both liquid-liquid and solid-liquid heterogeneous reaction mixtures. They are known to accelerate reaction rates by facilitating formation of interphase transfer of species and making reactions between reagents in two immiscible phases possible. Application of PTC instead of traditional technologies for industrial processes of organic synthesis provides substantial benefits for the environment. On the basis of numerous reports it is evident that phase-transfer catalysis is the most efficient way for generation and reactions of many active intermediates. In this review we report various uses of PTC in syntheses and reactions of five-membered heterocycles compounds and their multifused rings.

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“…Among the compounds, 4,4‐dibromo‐5‐pyrazolone have been reported as fungicides against Helminthosporium oryzae [2], α‐glucosidase inhibitors, and used for the treatment of tumor metastasis, AIDS, diabetes, hyperlipidemia, autoimmune disease, allergy, and rejection in organ transplant [3]. They are also useful synthetic intermediates for the preparation of diazo‐dyes [4], and fused‐ [5] and spiro‐hetercyclic compounds [6].…”

Section: Introductionmentioning

confidence: 99%