Expedient Preparation of 2-(5,6-Dihydro-4H-1,3-oxazin-2-yl)anilines

Michael Rosana, Chemistry (on left in photo)

Faculty Mentor:  Dr. David A. Hunt

              The research conducted this summer at the College of New Jersey is based on previous work from the Hunt lab which focused on a novel two-step, one pot synthesis of aryl-substituted oxazolines, a 5-membered heterocyclic ring system containing nitrogen and oxygen (n = 1), from isatoic anhydrides under mild, non-acidic conditions.  Previously, the standard method of synthesis called for harsh acidic reaction conditions requiring two separate steps.

              This summer, we have utilized this method to successfully prepare a series of oxazines (the corresponding 6-membered ring system) and are currently investigating the amenability of this method to make seven- (n = 2 ) and eight- (n = 3) membered heterocyclic rings.

              These compounds are of interest due their potential to function as metal chelating agents.  These can be used to remove metal ions from water for purification or from biological matrices, as in heavy metal poisoning.  Based on a myriad of possible substitutions, these compounds may also have other properties which could prove useful. 

Personal Statement

              Working in the research laboratory with Dr. Hunt and the other students and with the others involved with the SURP program has been a great experience.  I have made friendships that I am sure will carry on through into the new school year.  Along with friendships I have made, I have also learned a lot about lab procedure and lab techniques.  These will prove to be helpful in whatever profession I choose.  The lab work has also solidified my thinking that I would like to attend graduate school, which consists mostly of research towards a thesis.  The research experience itself also gives us the background that many graduate schools like to see, as those with prior research experience are more desirable.