Paper Information

Journal:   JOURNAL OF APPLIED RESEARCHES IN CHEMISTRY (JARC)   SPRING 2010 , Volume 4 , Number 13; Page(s) 35 To 41.
 
Paper: 

SIO2/H2C2O4: AN EFFICIENT CATALYST FOR 1, 2, 3, 4- TETRAHYDRO -QUINOLINE SYNTHESIS BY IMINO DIELS-ALDER REACTION

 
 
Author(s):  SHOUSHIZADEH M.R.*, MEHRABIAN M.
 
* DEPARTMENT OF MEDICINAL CHEMISTRY, COLLEGE OF PHARMACY, AHVAZ JUNDISHAHPOUR UNIVERSITY OF MEDICAL SCIENCE, AHVAZ, IRAN
 
Abstract: 

Tetrahydroquinoline derivatives are widely found in many natural products, which exhibit various biological activities. For the synthesis of tetrahydroquinolines, the imino Diels-Alder reaction of N-arylimine with olefins is highly efficient. In recent years, great efforts have been made to develop organic reactions in an environment-friendly manner (green chemistry).
In this research Oxalic acid /Silica Gel was found to be an efficient catalyst for the imino Diels-Alder (povarov) reaction of synthesized N-aryl-substituted aldimines and various alkenes to provide tetrahydroquinolines in good yields. The influence of the loading of oxalic acid, the structure of imines and alkenes was studied. Mild reaction conditions, facile experimental procedure, low price of oxalic acid and Silica Gel and good yields of products render this new method attractive for practical synthesis of many tetrahydroquinoline derivatives.

 
Keyword(s): TETRAHYDROQUINOLINE, IMINO DIELS- ALDER, OXALIC ACID / SILICA GEL, N-ARYLIMINE, NAPHTHOQUINONE, BENZOQUINONE, MALEIC ANHYDRIDE
 
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