ORGN 337 |
Solution-phase parallel synthesis of spirohydantoins derivatives
| Marcelo J. Nieto, Ashok E. Phillip, Azadeh Mirbagheri, and Christopher R. McCurdy. Department of Medicinal Chemistry and Laboratory for Applied Drug Design and Synthesis, University of Mississippi, School of Pharmacy, University, MS 38677 |
The spirohydantoin (3) is an attractive scaffold for the preparation of libraries of compounds with possible analgesic activity. The spirohydantoin is considered as a “priviledged G-protein receptor structure” and only few modifications have been reported. A solution-phase parallel synthesis was developed to prepare a library of spirohydantoins. In the first step the Strecker reaction was successfully used in the transformation of the N-substituted piperidone (1) to an a-amino nitrile with aniline and KCN (or TMSCN) to obtain a-anilino nitrile piperidine (2). This intermediate was reacted with a diverse set of isocyanates followed by the cyclization in refluxing acidic conditions to yield the desired library of compounds. |
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Physical Organic, Combinatorial, Materials, Molecular Recognition
8:00 PM-10:00 PM, Tuesday, March 30, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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