Vahid Khakyzadeh1, Mohammad Ali Zolfigol2, Fatemeh Derakhshan-Panah3, Majid Jafarian4, Mir Vahid Miri4, Maryam Gilandoust5. 1. Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, 15418, Iran. v.khakyzadeh@kntu.ac.ir. 2. Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 6517838683, Hamedan, Iran. zolfi@basu.ac.ir. 3. Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 6517838683, Hamedan, Iran. 4. Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, 15418, Iran. 5. Department of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore, Karnataka, India.
Abstract
The aim of this work is to introduce, model, and optimize a new non-acid-catalyzed system for a direct N[Formula: see text]N-C bond formation. By reacting naphthols or phenol with anilines in the presence of the sodium nitrite as nitrosonium ([Formula: see text] source and triethylammonium acetate (TEAA), a N[Formula: see text]N-C group can be formed in non-acid media. Modeling and optimization of the reaction conditions were investigated by response surface method. Sodium nitrite, TEAA, and water were chosen as variables, and reaction yield was also monitored. Analysis of variance indicates that a second-order polynomial model with F value of 35.7, a P value of 0.0001, and regression coefficient of 0.93 is able to predict the response. Based on the model, the optimum process conditions were introduced as 2.2 mmol sodium nitrite, 2.2 mL of TEAA, and 0.5 mL [Formula: see text] at room temperature. A quadratic (second-order) polynomial model, by analysis of variance, was able to predict the response for a direct N=N-C group formation. Predicted response values were in good agreement with the experimental values. Electrochemistry studies were done to introduce new Michael acceptor moieties. Broad scope, high yields, short reaction time, and mild conditions are some advantages of the presented method.
The aim of this work is to introduce, model, and optimize a new non-acid-catalyzed system for a direct N[Formula: see text]n class="Chemical">N-C bond formation. By reacting naphthols or phenol with anilines in the presence of the sodium nitrite as nitrosonium ([Formula: see text] source and triethylammonium acetate (TEAA), a N[Formula: see text]N-C group can be formed in non-acid media. Modeling and optimization of the reaction conditions were investigated by response surface method. Sodium nitrite, TEAA, and water were chosen as variables, and reaction yield was also monitored. Analysis of variance indicates that a second-order polynomial model with F value of 35.7, a P value of 0.0001, and regression coefficient of 0.93 is able to predict the response. Based on the model, the optimum process conditions were introduced as 2.2 mmol sodium nitrite, 2.2 mL of TEAA, and 0.5 mL [Formula: see text] at room temperature. A quadratic (second-order) polynomial model, by analysis of variance, was able to predict the response for a direct N=N-C group formation. Predicted response values were in good agreement with the experimental values. Electrochemistry studies were done to introduce new Michael acceptor moieties. Broad scope, high yields, short reaction time, and mild conditions are some advantages of the presented method.
Entities:
Keywords:
Direct N=N–C bond formation; Electrochemistry; Green process; Modeling; Optimization
Authors: B J Dezube; T A Dahl; T K Wong; B Chapman; M Ono; N Yamaguchi; S D Gillies; L B Chen; C S Crumpacker Journal: J Infect Dis Date: 2000-07-28 Impact factor: 5.226