9-Anthraldehyde oxime: a synthetic tool for variable applications
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REVIEW
9‑Anthraldehyde oxime: a synthetic tool for variable applications Sarbast M. Ahmed1 · Faiq H. S. Hussain2 · Paolo Quadrelli3 Received: 15 April 2020 / Accepted: 23 September 2020 © The Author(s) 2020
Abstract Oximes are one of the most important and prolific functional groups in organic chemistry; among them, 9-anthraldehyde oxime represents a valuable example both from the preparative side and the synthetic applications. There are many strategies to prepare 9-anthraldehyde oxime from different functional groups that were summarized in the present review, focusing on the most recent and innovative. The main synthetic applications of 9-anthraldehyde oxime are presented and thoroughly discussed, focusing on the most recent and innovative synthetic strategies. Graphic abstract O
H tBu MeO
N
R
O
O N
O N
O
R'
Me
N
O N
N O
H
O O
N
CN
OH
N O N Boc
O
NH 2 OC NH 2
O O N
O N
OMe
R
OH OH
O
O
N
C
S
OC
CO Os COOC
CO Os N
CO
CO CO
Os
CO CO
N H
O
(S)
O O N
O N
O
O
OH
O
Keywords Anthracene aldehyde · Oxime · Synthesis · Synthetic applications
Introduction Oximes represent an important and interesting class of organic compounds, with a wide range of applications [1]; typically, protection, purification, and characterization of carbonyl compounds are the traditional uses of these derivatives [2]. In addition, they can be converted into nitriles, nitro compounds, nitrones, amines, amides and they can also be exploited in the synthesis of azaheterocycles. 9-Anthraldehyde oxime (CAS n° 34810-13-4) has not been studied so far; therefore a limited or very few publications describe * Paolo Quadrelli [email protected] 1
Department of Pharmaceutical Chemistry, Pharmacy College, Hawler Medical University, Erbil, Kurdistan Region, Iraq
2
Medical Analysis Department, Faculty of Science, Tishk International University, Erbil, Kurdistan Region, Iraq
3
Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia,, Italy
the uses of this molecule in organic chemistry. 9-Anthraldehyde oxime is a primary material for the preparation of a large number of cyclic and heterocyclic compounds, for instance, isoxazoles, isoxazolines, isoxazolidines, as well as organic compounds such as aldehydes, amides, amines, and nitriles. This review will cover a research area whose impact in current organic synthesis can be evaluated from Fig. 1 that reports the literature dealing with the main topics that compose the present work. 9-Anthraldehyde oxime is a commercially available product that was first synthesized by Hinkel and co-authors [3] in 1935 (m.p. 186–187 °C). In repeating the preparation of the same compound by Fieser and Hartwell used a different procedure that afforded the desired compound in 93% yield with a different melting point of 165 °C [4]. Meek and Dann [5] prepared both the syn- and antiisomer of 9-anthraldehyde oxime (Fig. 2) through another different procedure; they first repeated the Fieser’s procedure by neutralizing hydroxylamine with sodium car
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