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

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Abstract

[Figure not available: see fulltext.] 1,2,4-Oxadiazoles are heterocycles characterized by low aromaticity and the presence of a weak OâN 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 BoultonâKatritzky Rearrangement (BKR), Migration â Nucleophilic Attack â 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.
Lingua originaleEnglish
pagine (da-a)936-947
Numero di pagine12
RivistaChemistry of Heterocyclic Compounds
Volume53
Stato di pubblicazionePublished - 2017

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Oxadiazoles
Heterocyclic Compounds
Nucleophiles
Cyclization

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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title = "Rearrangements of 1,2,4-Oxadiazole: {"}One Ring to Rule Them All{"}",
abstract = "[Figure not available: see fulltext.] 1,2,4-Oxadiazoles are heterocycles characterized by low aromaticity and the presence of a weak O{\^a}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{\^a}Katritzky Rearrangement (BKR), Migration {\^a} Nucleophilic Attack {\^a} 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.",
keywords = "1, 2, 4-oxadiazole; ANRORC; Boulton{\^a}€“Katritzky rearrangement; heterocyclic rearrangement; photochemistry; Organic Chemistry",
author = "Silvestre Buscemi and {Palumbo Piccionello}, Antonio and Andrea Pace",
year = "2017",
language = "English",
volume = "53",
pages = "936--947",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer New York",

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TY - JOUR

T1 - Rearrangements of 1,2,4-Oxadiazole: "One Ring to Rule Them All"

AU - Buscemi, Silvestre

AU - Palumbo Piccionello, Antonio

AU - Pace, Andrea

PY - 2017

Y1 - 2017

N2 - [Figure not available: see fulltext.] 1,2,4-Oxadiazoles are heterocycles characterized by low aromaticity and the presence of a weak OâN 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 BoultonâKatritzky Rearrangement (BKR), Migration â Nucleophilic Attack â 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.

AB - [Figure not available: see fulltext.] 1,2,4-Oxadiazoles are heterocycles characterized by low aromaticity and the presence of a weak OâN 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 BoultonâKatritzky Rearrangement (BKR), Migration â Nucleophilic Attack â 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.

KW - 1

KW - 2

KW - 4-oxadiazole; ANRORC; Boulton–Katritzky rearrangement; heterocyclic rearrangement; photochemistry; Organic Chemistry

UR - http://hdl.handle.net/10447/252661

UR - http://www.springerlink.com/content/0009-3122

M3 - Article

VL - 53

SP - 936

EP - 947

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

ER -