Reaction of 4-nitro-1,2-phenylenedl4mine with 1-(4-R-phenyl)-3-(4-nitrophenyl)propenones

Kolos, N. N.; Orlov, V. D.; Arisa, D.; Шишкин, Олег В.; Struchkov, Yu. T.; Vorob'eva, N. P.

doi:10.1007/bf01169360

Cited by 7 publications

(6 citation statements)

References 1 publication

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“…Such a hypothesis is in good agreement with the data obtained by us previously for reactions of enones with a series of azabinucleophiles [9][10][11].…”

supporting

confidence: 88%

Investigations on 5-(2-aryl-2-oxo-ethylidene)-1,3-dimethylbarbituric and thiobarbituric acids: reactions with thioureas and thioacetamide

Kolos

Zamigaylo

Мусатов

2009

Chem Heterocycl Comp

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Keywords: 5-(2-amino-4-arylthiazol-5-yl)-6-hydroxy-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones, 5-(2-amino-4-arylthiazol-5-yl)-1,3-dimethylpyrimidine-2,4-diones, 5-(2-aryl-2-oxoethylidene)-1,3-dimethylbarbituric and 5-(2-aryl-2-oxoethylidene)thiobarbituric acids, thioacetamide, thioureas, one-pot synthesis, cyclocondensation.It is well known that heterocyclization involving α,β-unsaturated ketones and thioureas is a convenient method of synthesis of 3,4-dihydropyrimidine-2-thiones [1-3]. However an alternative direction is also mentioned in the literature for the interaction of α,β-unsaturated ketones with thioureas leading to the formation of a dihydrothiazine ring. Nucleophilic addition of mercapto group with subsequent cyclization is characteristic of cyclic unsaturated ketones [4,5], and also on using N-arylthioureas in the reaction [6,7]. N N Me O Me O N NH Ar O R O N N O Me O Me O N N Me Ar O Me 4 5 R = H, Ar

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“…Such a hypothesis is in good agreement with the data obtained by us previously for reactions of enones with a series of azabinucleophiles [9][10][11].…”

supporting

confidence: 88%

Investigations on 5-(2-aryl-2-oxo-ethylidene)-1,3-dimethylbarbituric and thiobarbituric acids: reactions with thioureas and thioacetamide

Kolos

Zamigaylo

Мусатов

2009

Chem Heterocycl Comp

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“…For the background to chalcones, see: Awad et al (1960); Coudert et al (1988); Insuasty et al (1992Insuasty et al ( , 1997; Kolos et al (1996); Samshuddin et al (2010); Fun et al (2010); ; Shettigar et al (2010); Sharma et al (1997); Ravishankar et al (2003Ravishankar et al ( , 2005; Butcher et al (2006); Narayana et al (2007); Sarojini et al (2007a,b); Jasinski et al (2011). For bond-length data, see: Allen et al (1987).…”

Section: Related Literaturementioning

confidence: 99%

“…Chalcones (1,3-diarylpropenones) have been widely used as starting materials in numerous synthetic reactions (Awad et al, 1960;Coudert et al, 1988) including the preparation of fused ring heterocyclic compounds (Insuasty et al, 1992(Insuasty et al, , 1997Kolos et al, 1996;Samshuddin et al, 2010;Fun et al, 2010). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al, 2006;Shettigar et al, 2010).…”

Section: S1 Commentmentioning

confidence: 99%

(2E)-3-[3-(Benzyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one

Fun

Loh

Sarojini³

et al. 2011

Acta Cryst E

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In the title compound, C22H18O3, an intramolecular O—H⋯O hydrogen bond stabilizes the molecular structure, forming an S(6) ring motif. The central benzene ring forms a dihedral angle of 64.74 (5)° with the phenyl ring and a dihedral angle of 5.58 (5)° with the terminal benzene ring. In the crystal, molecules are linked into columns along the a axis via intermolecular C—H⋯O hydrogen bonds. C—H⋯π interactions involving the centroid of the hydroxy-substituted benzene ring further stabilize the crystal structure.

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“…For general background and applications of chalcones, see: Awad et al (1960); Coudert et al (1988); Insuasty et al (1992Insuasty et al ( , 1997; Kolos et al (1996); Sarojini et al (2006); Shettigar et al (2010); Samshuddin et al (2010); Fun et al (2010). For related structures, see: Butcher et al (2006); Ravishankar et al (2003Ravishankar et al ( , 2005; Narayana et al (2007); Sarojini, Narayana et al (2007); ; Sharma et al (1997); Jasinski et al (2011).…”

Section: Related Literaturementioning

confidence: 99%

(2E)-3-(3-Benzyloxyphenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one

Fun

Arshad

Sarojini³

et al. 2011

Acta Cryst E

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In the molecule of the title compound, C23H20O3, an intramolecular O—H⋯O hydrogen bond generates an S(6) ring. The central benzene ring makes dihedral angles of 80.17 (8) and 16.99 (7)°, respectively, with the benzyloxy and hydroxymethyl phenyl rings. In the crystal, molecules are linked via intermolecular C—H⋯O hydrogen bonds to form dimers. The dimers are connected by C—H⋯O hydrogen bonds and C—H⋯π interactions to form columns down the b axis.

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Reaction of 4-nitro-1,2-phenylenedl4mine with 1-(4-R-phenyl)-3-(4-nitrophenyl)propenones

Cited by 7 publications

References 1 publication

Investigations on 5-(2-aryl-2-oxo-ethylidene)-1,3-dimethylbarbituric and thiobarbituric acids: reactions with thioureas and thioacetamide

Investigations on 5-(2-aryl-2-oxo-ethylidene)-1,3-dimethylbarbituric and thiobarbituric acids: reactions with thioureas and thioacetamide

(2E)-3-[3-(Benzyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one

(2E)-3-(3-Benzyloxyphenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one

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