4-Aryldihydropyrimidines via the Biginelli Condensation: Aza-Analogs of Nifedipine-Type Calcium Channel Modulators

Kappe, C. Oliver

doi:10.3390/30100001

Cited by 148 publications

(51 citation statements)

References 29 publications

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“…The reaction mixture was kept overnight and the precipitate obtained was filtered and the compound was recrystallized with ethanol in good yield. 25 The treatment of 1 with α-haloester in ethanol under reflux for about 6 h and 12 h afforded 3(a-i) as shown in scheme 1 and 5(a-m) as shown in scheme 2 respectively. The proposed mechanism for the above reaction is given in scheme 3.…”

Section: Synthesismentioning

confidence: 99%

Synthesis, characterization and biological evaluation of thiazolopyrimidine derivatives

2012

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Abstract. Different substituted diesters of thiazolopyrimidine were prepared by the treatment of 3,4 dihydropyrimidine2-thione with α-haloesters using ethanol under reflux condition affording 71-85% yield. IR, 1 HNMR, 13 CNMR and elemental analyses were used for the characterization of these compounds. The crystal and molecular structure of one of the product, 5-phenyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-2,6-dicarboxylic acid diethyl ester (3e) was verified by single crystal X-ray diffraction method. The antimicrobial activity was evaluated against four bacterial strains and one fungal species. Few of the derivatives exhibited antibacterial and antifungal activities.

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Section: Synthesismentioning

confidence: 99%

Synthesis, characterization and biological evaluation of thiazolopyrimidine derivatives

2012

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“…Many substituted pyrimidine rings play an important role as analgesic, antipyretic, antihypertensive and anti-inflammatory drugs also as pesticides, herbicides, plant growth regulators and organic calcium channel modulators. [1][2][3][4][5][6][7] Various synthesis methods have been reported in the literature for pyrimidine derivatives. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Most of them are based on the simple Biginelli three component cyclocondensation reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some Novel Pyrimidine Derivatives and Investigation of their Electrochemical Behavior

Akbaş¹,

Levent²,

Gümüş³

et al. 2010

Bulletin of the Korean Chemical Society

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2-Iminopyrimidines (1a-e) and 2-thioxopyrimidine (2) were synthesized using the Biginelli three component cyclocondensation reaction of an appropriate β-diketone, arylaldehyde, and guanidine (for 1a-e) or thiourea (for 2). The electrochemical properties of the novel systems were investigated by CV and DPV. Moreover, B3LYP/6-31G(d,p) method was applied to the present structures in order to gather some structural and physicochemical data.

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“…This 'aryl-group up' configuration is considered crucial for the enhanced calcium antagonist activity in this compound 12 . The 4-aryl substituent (methoxy group) adopts a synperiplanar conformation with respect to C4-H4 bond.…”

Section: Crystallographymentioning

confidence: 99%

Synthesis and Crystal Structure Analysis of Ethyl-4-(4-acetoxy-phenyl)-3-acetyl-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate

Nagarajaiah¹,

Begum²

2012

Chem Sci Trans

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4-(4-Acetoxy-phenyl)-3-acetyl-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (2) was synthesized by a two step reaction process. Preliminary spectroscopic analysis was done by IR, 1 HNMR and elemental analysis. The crystal and molecular structure was further confirmed using single crystal x-ray diffraction. The dihedral angle between the planes of the aryl and dihydropyrimidine rings is 89.65(6)°, which is almost orthogonal. The dihydropyrimidine ring adopts twist-boat conformation. The crystal structure is stabilized by C-H…O, N-H…S and C-H…π interactions.

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4-Aryldihydropyrimidines via the Biginelli Condensation: Aza-Analogs of Nifedipine-Type Calcium Channel Modulators

Abstract: Recent results from the author's laboratory in the area of dihydropyrimidine chemistry are summarized

Cited by 148 publications

References 29 publications

Synthesis, characterization and biological evaluation of thiazolopyrimidine derivatives

Synthesis, characterization and biological evaluation of thiazolopyrimidine derivatives

Synthesis of Some Novel Pyrimidine Derivatives and Investigation of their Electrochemical Behavior

Synthesis and Crystal Structure Analysis of Ethyl-4-(4-acetoxy-phenyl)-3-acetyl-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate

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