Facile synthesis of <i>N,N</i>‐dialkylselenoamides from amides

Koketsu, Mamoru; Okayama, Yoshihiro; Aoki, Hiroshi; Ishihara, Hideharu

doi:10.1002/hc.10016

Cited by 27 publications

(9 citation statements)

References 33 publications

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“…Very recently, the group of Koketsu and other groups reported on the synthesis of some 1,3-selenazolidine-2-imines [22][23][24][25]. For example, N,N'-diisopropylselenourea (10) and 2-bromo-2-methylpropanoyl bromide (11) in pyridine led to the 2-imino-1,3-selenazolidin-4-one 12, the structure of which has been determined by X-ray crystallography [22] (Scheme 1).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of 1,3‐Selenazol‐2(3H)‐imines

Atanassov

Linden

Heimgartner

2010

Helvetica Chimica Acta

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The reaction of N,N′‐diarylselenoureas 16 with phenacyl bromide in EtOH under reflux, followed by treatment with NH3, gave N,3‐diaryl‐4‐phenyl‐1,3‐selenazol‐2(3H)‐imines 13 in high yields (Scheme 2). A reaction mechanism via formation of the corresponding Se‐(benzoylmethyl)isoselenoureas 18 and subsequent cyclocondensation is proposed (Scheme 3). The N,N′‐diarylselenoureas 16 were conveniently prepared by the reaction of aryl isoselenocyanates 15 with 4‐substituted anilines. The structures of 13a and 13c were established by X‐ray crystallography.

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Section: Methodsmentioning

confidence: 99%

“…For example, N,N'-diisopropylselenourea (10) and 2-bromo-2-methylpropanoyl bromide (11) in pyridine led to the 2-imino-1,3-selenazolidin-4-one 12, the structure of which has been determined by X-ray crystallography [22] (Scheme 1).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 1,3‐Selenazol‐2(3H)‐imines

Atanassov

Linden

Heimgartner

2010

Helvetica Chimica Acta

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“…N , N ‐Dialkylselenoamides 199 could be successfully synthesized from easily available N , N ‐dialkylamides 198 using oxalyl chloride as activating and chlorinating reagent which allowed N , N ‐dialkylamides to react with LiAlHSeH to yield the resulting compounds. Due to steric hindrance, the N , N ‐dialkylamides having bulky substituent groups could not be converted into their corresponding selenoamide derivatives (Scheme ) …”

Section: Preparation Of Imidoyl Chloridesmentioning

confidence: 99%

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Mohammadkhani

Heravi

2019

ChemistrySelect

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Oxalyl chloride, (COCl)2, as an inexpensive commercially available chemical is one of the most versatile applicable organic reagents in chemical transformations. It is also employed extensively in various chemical industries. It is employed in various chemical transformations such as chlorination, oxidation, reduction, dehydration, decarboxylation, and formylation reactions as well as ring cleavage of epoxides. During the past decades, numerous procedures using (COCl)2 as reagent have been developed and published. However, its importance has largely been overlooked by the absence of a comprehensive review in chemical literature dealing with its application in organic transformations and its utilization in the chemical industry. This Review aims to provide an overview for the applications of oxalyl chloride in organic synthesis, including its physical properties, synthesis, as well as its unique roles as the reagent in organic reactions, covering the literature over the past 103 years (from 1916 to date).

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“…The secondary and tertiary selenoamides could be obtained by reaction of amides with appropriate selenating reagents such as LiAlHSeH (prepared from LiAlH 4 /Se), a mixture of ( i Bu 2 AlSe) 2 and ( i BuAlSe)n (prepared from i Bu 2 AlH/Se), (Me 2 Al) 2 Se (prepared from R 3 SnSeSnR 3 /Me 3 Al), selenium-Lawesson's reagent and (Et 4 N) 2 WSe 4[91][92][93][94][95] (Scheme 33).…”

mentioning

confidence: 99%