Cyclization and Cycloisomerization of π-Tethered Ynamides: An Expedient Synthetic Method to Construct Carbo- and Heterocycles

Dedicated to Professor S. V. Kessar, Punjab University, India, for his outstanding contribution in the area of synthetic ­organic chemistry and also on the occasion of his 85^th birthday

Abstract

Stable ynamides are used for the development of novel synthetic transformations and the construction of unusual carbo/heterocycles. The intramolecular cyclization of π-tethered alkene/alkyne/allene-ynamides is studied extensively for the fabrication of a wide range of molecular scaffolds for various applications. The ketene-acetal/aminal generated in situ from π-tethered ynamides participates in intramolecular cyclization/cycloisomerization processes to yield N-bearing fused heterocycles. This account summarizes the scientific merits and the advances made in cyclization and cycloisomerization strategies for stable π-tethered alkene/alkyne/allene-ynamides.

1 Introduction

2 π-Tethered Ynamides

3 Alkene-Tethered Ynamides

4 Alkyne-Tethered Ynamides

5 Allene-Tethered Ynamides

6 Concluding Remarks

Key words

ynamides - cycloisomerization - cycloaddition - ring-closing metathesis - cyclopropanation - carbenes - radical cyclization - heterocycles

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