Rearrangements of 1,2,4-Oxadiazole: "One Ring to Rule Them All"

被引：42

作者：

Piccionello, Antonio Palumbo ^{[1
]}

Pace, Andrea ^{[1
]}

Buscemi, Silvestre ^{[1
]}

机构：

[1] Univ Palermo, Dipartimento Sci & Tecnol Biol Chim & Farmaceut S, Viale Sci Ed 17, I-90128 Palermo, Italy

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2017年 / 53卷 / 09期

关键词：

1,2,4-oxadiazole; ANRORC; Boulton-Katritzky rearrangement; heterocyclic rearrangement; photochemistry; FLUORINATED HETEROCYCLIC-COMPOUNDS; BOULTON-KATRITZKY REACTION; ANRORC-LIKE REARRANGEMENT; MONONUCLEAR REARRANGEMENT; SIDE-CHAIN; IONIC LIQUID; DFT; OXADIAZOLES; DERIVATIVES; ACID;

D O I：

10.1007/s10593-017-2154-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2,4-Oxadiazoles are heterocycles characterized by low aromaticity and the presence of a weak O-N bond and are widely studied due to their tendency to rearrange into more stable heterocyclic compounds. This review covers literature from the last fifteen years, highlighting the general features of 1,2,4-oxadiazoles and their applications. Regarding the reactivity, the development of classical reactions (thermal and photochemical rearrangements) is presented in terms of synthetic utility and mechanistic insight. Among the relevant rearrangement reactions, the Boulton-Katritzky Rearrangement (BKR), Migration - Nucleophilic Attack - Cyclization (MNAC), and Addition of the Nucleophile, Ring Opening, and Ring Closure (ANRORC) reactions are discussed, together with recent noteworthy syntheses and applications of the 1,2,4-oxadiazole ring.

引用

页码：936 / 947

页数：12

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