Synthesis of 4-Aryl-2-imino-2<i>H</i>-selenazolines by a Reaction of α α-(Selenocyanato)acetophenones With Anilines

Bodtke, Anja; Kandt, Madeleine; Pfeiffer, W.‐D.; Langer, Peter

doi:10.1080/10426500600892685

Cited by 7 publications

(2 citation statements)

References 27 publications

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“…We have developed a synthesis of 4-aryl-2-imino-2 H -selenazolines 20a – f , albeit in low isolated yields, by cyclization of anilines 19a – c with α-(selenocyanato)acetophenones 18a – d which were prepared by reaction of the corresponding phenacyl bromides with KSeCN (Scheme 13 ). 19 The formation of the products can be explained by attack of the amine to the nitrile (intermediate A ) and subsequent cyclization by attack of the nitrogen atom to the carbonyl group. Hydroxylamine ( 19d ) could also successfully be employed in this reaction to give 4-hydroxy-2-imino-2 H -selenazoline 20g in 17% yield.…”

Section: -Amino-13-selenazolesmentioning

confidence: 99%

Adventures in 1,3-Selenazole Chemistry

Langer

2021

Synlett

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The synthesis of 1,3-selenazoles and related compounds, including 2,4,5-trisubstituted, 2,4-disubstituted, 4,5-disubstituted, 4-substituted 1,3-selenazoles, and parent unsubstituted 1,3-selenazole, is highlighted. Emphasis is also given on 2-benzoyl-1,3-selenazoles which can be functionalized by Knoevenagel reactions or by rearrangements via their corresponding oximes. Syntheses of bis-, tris-, and tetrakis(1,3-selenazoles) are discussed as well. 1,3,4-6H-Selenadiazines are available from selenosemicarbazides and can undergo ring-contraction or deselenation reactions. Most syntheses rely on the application of selenocarboxylic amides, selenourea and related building blocks which are conveniently available by reaction of the corresponding oxygen analogues with P4Se10.1 Introduction2 Selenocarboxylic Amides3 2,4,5-Tri- and 2,4-Disubstituted 1,3-Selenazoles4 Bis(1,3-selenazoles)5 2-Amino-1,3-selenazoles6 2-Unsubstituted 1,3-Selenazoles7 1,3,4-Selenadiazines8 Conclusions

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Section: -Amino-13-selenazolesmentioning

confidence: 99%

Adventures in 1,3-Selenazole Chemistry

Langer

2021

Synlett

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“…Of the vast number of organoselenium compounds, the organo-selenocyanate derivatives have shown considerable potential as active intermediates in organic synthesis and have been extensively studied for their anticancer properties besides other important biological activities . In particular, the α-carbonyl selenocyanates are considered to be synthetically important since the presence of the carbonyl and cyano functions serve as the basic scaffold for the construction of an array of selenium containing heterocycles and other selenoorganic compounds . Surprisingly only scanty reports are available in the literature for the synthesis of α-carbonyl selenocyanates. ,− The few reported methods includes the synthesis of α-carbonyl selenocyanates from aromatic alkenes, α-haloketones, or aryl ketones using selenocyanate salts as the selenocyanate source (Scheme a).…”

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confidence: 99%

Selenocyanation of Aryl and Styryl Methyl Ketones in the Presence of Selenium Dioxide and Malononitrile: An Approach for the Synthesis of α-Carbonyl Selenocyanates

et al. 2020

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Visible Light and Triselenium Dicyanide (TSD): New Horizons in the Synthesis of Organic Selenocyanates

Anghinoni

Ferreira

Piquini

et al. 2023

Chemistry A European J

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Herein we describe a new method for the synthesis of α‐carbonyl selenocyanates by reacting triselenium dicyanide (TSD) and styrenes under blue light irradiation and O2 atmosphere. The reactions are triggered by the formation of Se‐centered radical species, followed by the addition/oxidation of the styrene π‐bond. α‐Carbonyl selenocyanates and α‐hydroxy selenocyanates were obtained in moderate to excellent yields from aryl‐ and alkyl‐substituted alkenes, respectively. It was demonstrated that α‐carbonyl selenocyanates could be used as a synthetic platform in a multicomponent reaction strategy to prepare 2‐phenylimidazo[1,2‐a]pyridine derivatives, which were evaluated for their photophysical properties. Overall, this new method provides a useful tool for synthesizing α‐carbonyl selenocyanates, demonstrating their potential for use in the synthesis of other compounds, and opening new synthetic opportunities to construct organic selenocyanate compounds.

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Synthesis of 4-Aryl-2-imino-2H-selenazolines by a Reaction of α α-(Selenocyanato)acetophenones With Anilines

Cited by 7 publications

References 27 publications

Adventures in 1,3-Selenazole Chemistry

Adventures in 1,3-Selenazole Chemistry

Selenocyanation of Aryl and Styryl Methyl Ketones in the Presence of Selenium Dioxide and Malononitrile: An Approach for the Synthesis of α-Carbonyl Selenocyanates

Visible Light and Triselenium Dicyanide (TSD): New Horizons in the Synthesis of Organic Selenocyanates

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