Reactions with α-substituted cinnamonitriles

Abdel‐Fattah, Azza M.; Hussain, S. M.; El‐Reedy, A. M.; Yousif, N. M.

doi:10.1016/s0040-4020(01)91566-2

Cited by 21 publications

(7 citation statements)

References 3 publications

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“…Remarkably, these [1,2]-dihydro compounds remained stable at room temperature over a period of weeks, despite the loss of aromaticity following the addition of the Grignard reagent. Some aryl- 22 and ferrocenylsubstituted 23 examples appear to share the same stability shown by our nitrile-substituted structures, whereas Lyle 24 has reported instability in the cyano-substituted dihydropyridine analogues.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Unusual Nucleophilic Addition of Grignard Reagents in the Synthesis of 4-Amino-pyrimidines

et al. 2018

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Pyrimidines have always received considerable attention because of their importance in synthesis and elucidation of biochemical roles, in particular that of vitamin B1. Herein, we describe a reaction pathway in a Grignard reagent-based synthesis of substituted pyrimidines. A general synthesis of α-keto-2-methyl-4-amino pyrimidines and their C6-substituted analogues from 4-amino-5-cyano-2-methylpyrimidine is reported. The presence of the nitrile substituent in the starting material also results in an unusual reaction pathway leading to C6-substituted 1,2-dihydropyrimidines. Grignard reagents that give normal pyrimidine products under standard reaction conditions can be switched to give dihydropyrimidines by holding the reaction at 0 °C before quenching.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Unusual Nucleophilic Addition of Grignard Reagents in the Synthesis of 4-Amino-pyrimidines

et al. 2018

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“…The synthesis of substituted aryl pyrimidines from α-substituted cinnamonitrile derivatives and benzamidine hydrochloride has been previously reported [21,22]. Although very early we have reported the synthesis of aminocyano substituted pyrimidines from the corresponding 4H-pyrans [23], the procedure now reported is, to the best of our knowledge, a new approach to the synthesis of a pyrimidine ring with a different substitution pattern.…”

Section: Introductionmentioning

confidence: 88%

One‐step synthesis of aminopyrimidines from 5‐Oxo‐4H‐benzopyrans

Salfrán¹,

Seoaneb²,

Suárez

et al. 2004

Journal of Heterocyclic Chem

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Section: Introductionmentioning

confidence: 93%

One‐Step Synthesis of Aminopyrimidines from 5‐Oxo‐4H‐Benzopyrans.

et al. 2004

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Novel 4-amino-6-aryl-2-phenylpyrimidine-5-carbonitriles have been prepared in one step procedure from the readily available 4-aryl-2-amino-3-cyano-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-benzopyrans. The mass spectroscopy study under EI conditions shows molecular peaks with high intensity corresponding to the loss of benzonitrile from the C2 position of the pyrimidine ring. Semiempirical (AM1 and PM3) and ab initio HF/6-31G* calculations reveal a favored distorted geometry where the three rings are not in the same plane.

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Reactions with α-substituted cinnamonitriles

Cited by 21 publications

References 3 publications

Unusual Nucleophilic Addition of Grignard Reagents in the Synthesis of 4-Amino-pyrimidines

Unusual Nucleophilic Addition of Grignard Reagents in the Synthesis of 4-Amino-pyrimidines

One‐step synthesis of aminopyrimidines from 5‐Oxo‐4H‐benzopyrans

One‐Step Synthesis of Aminopyrimidines from 5‐Oxo‐4H‐Benzopyrans.

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