Accession Number:

ADA220856

Title:

New Synthetic Methods. A. Lithiation of Methoxypyridines and N-Methylindoles Directed by a-Amino Alkoxides. B. Synthetic Methods Using N-Acyliminium Ions and 1-Acylpyridinium Salts

Descriptive Note:

Doctoral thesis

Corporate Author:

AIR FORCE INST OF TECH WRIGHT-PATTERSON AFB OH

Personal Author(s):

Report Date:

1990-01-01

Pagination or Media Count:

154.0

Abstract:

Nitrogen heterocycles have been widely studied and used in the synthesis of numerous alkaloids. Their importance as precursors to many biologically active compounds has focused a tremendous amount of attention on developing methods to functionalize these systems. In this study we investigated novel synthetic methods for regio- andor stereoselective carbon-carbon bond formation on the pyridine, indole, pyrrolidine, pyrrolidinone, and piperidone ring systems. In part A we report the regioselective metalation of several methoxypyridinecarboxaldehydes and 1-methylindole-2-carboxaldehydes using alpha-amino alkoxides as both a protecting and directing group. In part B we report the use of N-acyliminium ions and 1-acylpyridinium ions for the preparation of substituted pyridines and the asymmetric synthesis of dihydropyridones, pyrrolidines, pyrrolidinones, and piperidones.

Subject Categories:

  • Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE