DMF acetals as alkylating and cyclizing agents: A facile route to substituted pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-diones

Youssif, Shaker

doi:10.1007/bf00806857

Cited by 16 publications

(8 citation statements)

References 10 publications

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“…Treatment of the products with trichloroacetic and hydrochloric acids (ethanol, room temperature, 15 min) gave rise to a ring closure with the loss of one mole of acetophenone and dimethylamine, affording 7-methylpyrazolo [3,4-d]pyrimidine-4,6(5H)-dione (123) [78].…”

Section: Scheme 19mentioning

confidence: 99%

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Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis

Abu‐Shanab

Sherif

Mousa

2009

Journal of Heterocyclic Chem

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Section: Scheme 19mentioning

confidence: 99%

“…Treatment of compounds (77) with excess DMFDMA gave compounds (78), which was cyclized to pyrrole ring (79) under various condition, EtOH in the presence of HCl (method A), AcOH (method B), AcOH and Ac 2 O (method C), and (CF 3 CO) 2 O (method D) as shown in Scheme 15 [58][59][60].…”

Section: Preparation Of Heterocyclicmentioning

confidence: 99%

Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis

Abu‐Shanab

Sherif

Mousa

2009

Journal of Heterocyclic Chem

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“…The antitumor activity and the potential therapeutic applications of several pyrazolo[3,4-d]pyrimidine derivatives has also promped a more thorough investigation of these compounds (Youssif, 1997). Though chemical and physiological characteristics of these compounds are directly defined by the conformation of their molecules.…”

Section: Introductionmentioning

confidence: 99%

Crystal structure of 7-acetyl-5-benzoyl-6-phenyl-8-methyl-4,7-dihydropyrazolo[1,5-c]-1 H-pyrimidine-2-one

Akkurt¹,

Çeli̇k²,

İde³

et al. 2000

Zeitschrift Für Kristallographie - Crystalline Materials

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The title compound, C 22 H 19 N 3 O 3 crystallizes in the triclinic space group P " 1 with a 8X310(1) # e, b 9X890(1) # e, c 12X007(1) # e, a 92X17(1) , b 97X32(1) , g 106X72(1) ; Z 2; D x 1X3270(3) (g cm À3 ); R 0X068 for 1618 observed reflections [I ! 2s(I)]. The angle between the least squares planes formed by the N1± ±C2± ±N3 and C4± ±C5± ±C6 atoms of the pyrimidine ring is 30.1(3) . The dihydropyrimidine ring adopts a distorted boat conformation. The dihedral angle between the two phenyl rings is 48.4(1) . The pyrazole ring in the title compound is distorted from planarity with a maximum deviation of 0.153(3) # e for C4. Two molecules form a dimere with " 1. There are the shortest four inter-and two intramolecular hydrogen bonds in the structure and ffour intermolecular [N1± ±H1 0.860(3) # e,

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“…Dihydropyrazolo [1,5-c]pyrimidines have high physiological activity, the most important being cardiovascular activity [19]. Pyrazolo [3,4-d]pyrimidine systems possess a wide spectrum of biological activities, potential therapeutic applications and antitumor activity [20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical studies on the reactions of 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-one/-thione compounds with ethyl acetoacetate

et al. 2010

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The reaction of 1-amino-5-(4-methylbenzoyl)-4-(4-methylphenyl)pyrimidin-2(1H)-one/-thione (1a,b) with ethyl acetoacetate (EA) afforded moderate to good yields (59-63%) of ethyl 2-methyl-4-(4-methylbenzoyl)-5-(4-methylphenyl)-7-oxo/-thioxo-3,3a-dihydropyrazolo[1,5-c]pyrimidine-3-carboxylate (2a,b). The newly synthesized compounds were characterized by elemental analyses, IR, 1 H and 13 C NMR spectral data. All were compared with their previous analogues. The reaction mechanism of 1 with EA was studied by means of the B3LYP/6-31G(d,p) method. In addition, for reactants Fukui functions were performed using the data calculated with the Becke3-Lee-Yang-Parr (B3LYP) hybrid function.

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DMF acetals as alkylating and cyclizing agents: A facile route to substituted pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-diones

Cited by 16 publications

References 10 publications

Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis

Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis

Crystal structure of 7-acetyl-5-benzoyl-6-phenyl-8-methyl-4,7-dihydropyrazolo[1,5-c]-1 H-pyrimidine-2-one

Experimental and theoretical studies on the reactions of 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-one/-thione compounds with ethyl acetoacetate

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