Volume 31, Issue 51
Heterocyclic Compounds
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ChemInform Abstract: Synthesis of Conformationally Constrained Spirohydantoins with a Dibenzo[a,d]heptadiene Ring.

Bin Tao

Bin Tao

Dep. Chem., Univ. New Orleans, New Orleans, LA 70148, USA

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Jack W. Timberlake

Jack W. Timberlake

Dep. Chem., Univ. New Orleans, New Orleans, LA 70148, USA

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First published: 31 May 2010

Abstract

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ChemInform Abstract

Title compounds such as (IX) are prepared from dibenzosuberone (I) by transformation of an α-hydroxyester such as (III) to the corresponding azidoester (IV) followed by aminoester reduction and cyclization of the carbomethoxy asymmetric ureas thus prepared. Using a large excess of TFA in the transformation of (III), the unexpected ring expansion product (X) is formed.

chemical structure image

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