4.11 – 1,2,3-Triazoles and their Benzo Derivatives

Publisher Summary The 1,2,3-triazolines were first discovered during their studies on the action of organic azides on quinones. Triazolines have assumed considerable importance as intermediates in a number of organic syntheses and recently as a new class of potential anticonvulsant drugs. This chapter presents a comprehensive, unified survey of the methods of synthesis and reactions of Δ 2 -1,2,3-Triazolines. The chemistry of mono-, bi-, and polycyclic triazolines, and that of spiro- and bistriazolines, is considered. A brief account of the chemistry of Δ 3 - and Δ 4 -1,2,3-triazolines is given. Triazoline aromatization to triazoles is achieved by oxidation, isomerization reactions, and elimination of stable molecular fragments, all of which require the presence of free hydrogen at position 4 and/or 5 of the triazoline ring. The aromatization reaction affords a selective, synthetic route for the preparation of triazoles of definitive structure, in as much as azide addition to acetylenes is not regioselective.

Δ2-1,2,3-Triazolines

Die Chemie der in 7‐Stellung substituierten Norbornadiene; eine Untersuchung des sterischen Verlaufs einiger Additions‐Reaktionen ungesättigter Bicyclo[2.2.1]heptanderivate und über den Gültigkeitsbereich der Alderschen exo‐Regel

A. C. Oehlschlager

Papers

Bridged Ring Compounds. X.1,2 The Reaction of Benzenesulfonyl Azide with Norbornadiene, Dicyclopentadiene, and Bicyclo[2.2.2]-2-octene