This article is made freely available as part of this journal's Open Access. ID: | Niloofar ManuscriptRef.1-ajiras151016 |
Authors Affiliation:
1. University Sidi Mohamed Ben Abdellah | Faculty of Sciences Dhar El Mehraz | Department of Chemistry | Fez | Morocco |
1. University Sidi Mohamed Ben Abdellah | Faculty of Sciences Dhar El Mehraz | Department of Chemistry | Fez | Morocco |
Authors Copyright © 2016: | El Houssine Mabrouk 1 | and | Boukallaba Khalid 1 |
American Journal of Innovative Research & Applied Sciences
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| | ARTICLES | Am. J. innov. res. appl. sci. Volume 3, Issue 2, Pages 441-446 (November 2016) |
| Research Article SYNTHESIS OF NEW α-TETRAZOLYL α-AMINOESTERS DERIVATIVES | El Houssine Mabrouk | and | Boukallaba Khalid |. Am. J. innov. res. appl. sci. 2016; 3(2):141-146. | PDF FULL TEXT | |Received | 08 October 2016| |Accepted | 18 October 2016| |Published 25 October 2016 | |
| November | VOLUME 3 | N° 2 | 2016 |
ABSTRACT
Background: we report here our results concerning the synthesis of new racemic α-tetrazolyl α-carboxylic aminoesters, as methyl 2-benzamido-2-(5-methyltetrazol-1-yl)acetate, methyl 2-benzamido-2-(5-methyltetrazol-2-yl)acetate, methyl 2-benzamido-2-(5-(4-chlorophenyl)tetrazol-1-yl)acetate and methyl 2-benzamido-2-(5-(4-chlorophenyl)tetrazol-2-yl)acetate, with the aim to have access to new active biomolecules with a good yield through N-alkylation reaction. Objectives: α-Aminoesters possess a broad range of applications ranging from agrochemistry to medicine. We developed a simple, efficient, and environmentally benign method for the Synthesis of new racemic α-tetrazolyl α-carboxylic aminoesters derivatives by nucleophilic substitution of methyl α-azido glycinate N-benzoylated with various derivatives of 1H-tetrazole (HYPERLINK "http://www.sigmaaldrich.com/catalog/product/aldrich/347744?cm_sp=Insite-_-prodRecCold_xviews-_-prodRecCold10-4" 5-methyl-1H-tetrazole, p-chlorophenyl-1H-tetrazole). The structure of the these compounds have been characterized from the rigorous analysis of their spectral 1H-NMR, 13C-NMR and MS. Methods: The N-alkylation reactions of various derivatives of 1H-tetrazole nucleophiles with N-benzoylated methyl α-azido glycinates 1 are performed in different solvents (acetone and acetonitrile) for 24 h at room temperature in the presence of various bases (Et3N and DIEPA). Results: The products 2-3 were obtained with an improved overall yields (63-80%) by reaction of various derivatives of 1H-tetrazole Nu on azide derivative 1 and were characterized by MS, 1H-NMR and 13C-NMR spectroscopy. Conclusions: New racemic α-tetrazolyl α-carboxylic aminoesters were prepared by nucleophilic substitution of methyl α-azido glycinate N-benzoylated with various derivatives of 1H-tetrazole at room temperature under basic condition using diisopropylethylamine or triethylamine. The mild reaction conditions, utilization of an environmentally benign method, rapid conversion, very satisfactory yields, and wide applicability are the notable advantages of the present method.
Keywords: Tetrazole, Nucleophilic substitution, α-Aminoesters, Methyl α-azidoglycinate.
Background: we report here our results concerning the synthesis of new racemic α-tetrazolyl α-carboxylic aminoesters, as methyl 2-benzamido-2-(5-methyltetrazol-1-yl)acetate, methyl 2-benzamido-2-(5-methyltetrazol-2-yl)acetate, methyl 2-benzamido-2-(5-(4-chlorophenyl)tetrazol-1-yl)acetate and methyl 2-benzamido-2-(5-(4-chlorophenyl)tetrazol-2-yl)acetate, with the aim to have access to new active biomolecules with a good yield through N-alkylation reaction. Objectives: α-Aminoesters possess a broad range of applications ranging from agrochemistry to medicine. We developed a simple, efficient, and environmentally benign method for the Synthesis of new racemic α-tetrazolyl α-carboxylic aminoesters derivatives by nucleophilic substitution of methyl α-azido glycinate N-benzoylated with various derivatives of 1H-tetrazole (HYPERLINK "http://www.sigmaaldrich.com/catalog/product/aldrich/347744?cm_sp=Insite-_-prodRecCold_xviews-_-prodRecCold10-4" 5-methyl-1H-tetrazole, p-chlorophenyl-1H-tetrazole). The structure of the these compounds have been characterized from the rigorous analysis of their spectral 1H-NMR, 13C-NMR and MS. Methods: The N-alkylation reactions of various derivatives of 1H-tetrazole nucleophiles with N-benzoylated methyl α-azido glycinates 1 are performed in different solvents (acetone and acetonitrile) for 24 h at room temperature in the presence of various bases (Et3N and DIEPA). Results: The products 2-3 were obtained with an improved overall yields (63-80%) by reaction of various derivatives of 1H-tetrazole Nu on azide derivative 1 and were characterized by MS, 1H-NMR and 13C-NMR spectroscopy. Conclusions: New racemic α-tetrazolyl α-carboxylic aminoesters were prepared by nucleophilic substitution of methyl α-azido glycinate N-benzoylated with various derivatives of 1H-tetrazole at room temperature under basic condition using diisopropylethylamine or triethylamine. The mild reaction conditions, utilization of an environmentally benign method, rapid conversion, very satisfactory yields, and wide applicability are the notable advantages of the present method.
Keywords: Tetrazole, Nucleophilic substitution, α-Aminoesters, Methyl α-azidoglycinate.
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