A CAN-Induced Cyclodimerization-Ritter Trapping Strategy for the One-Pot Synthesis of 1-Amino-4-aryltetralins from Styrenes
Vijay Nair*, Roshini Rajan and Nigam P. Rath
*Organic Chemistry Division, Regional Research Laboratory (CSIR),
Trivandrum, India, and Department of Chemistry, University of Missouri, St.
Louis, Missouri 63121, Email: gvn
csrrltrd.ren.nic.in
V. Nair, R. Rajan, N. P. Rath, Org. Lett., 2002, 4, 1575-1577.
DOI: 10.1021/ol0257934
Abstract
A facile one-pot CAN-induced cyclodimerization of various styrenes in acetonitrile or acrylonitrile gave 1-amino-4-aryltetralin derivatives.
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proposed mechanism
Details
The document describes a novel one-pot synthesis method for 1-amino-4-aryltetralin derivatives using cerium(IV) ammonium nitrate (CAN)-induced cyclodimerization of styrenes in acetonitrile and acrylonitrile. This method builds on the foundational work of Heiba and Dessau on CAN-mediated carbon-carbon bond formation. The reaction involves the formation of a radical cation intermediate, which undergoes cyclization and subsequent trapping by the solvent, resulting in the formation of α-acetamido or α-acrylamido tetralin derivatives. The process is efficient, yielding diastereomers in significant quantities, and has been tested with various styrenes, producing consistent results. The synthesized α-aminotetralin derivatives are structurally similar to sertraline, a potent antidepressant, and exhibit important biological activities, including CNS stimulation, antibiotic, immunomodulatory, and antitumor properties. The study provides detailed spectroscopic data for the characterization of the products and proposes a mechanistic rationale for the reaction. Further research is ongoing to explore the reaction mechanism, expand its scope, and develop asymmetric synthesis methods. The findings are significant for the development of new therapeutic agents and the advancement of organic synthesis techniques.
Key Words
Ritter Reaction, Cerium Ammonium Nitrate
ID: J54-Y2002-780
