2008
DOI: 10.3987/com-07-11185
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N-Bromosuccinimide (NBS) as Promoter for Acylation of Sydnones in the Presence Acetic Anhydride under Neutral Conditions

Abstract: Various 4 -acetyl sydnones (2) can be prepared by reaction of the corresponding 3-aryl sydnones (1) with acetic anhydride at ~110 o C promoted by N-Bromosuccinimide (NBS) as an effective reagent for acylation of sydnones under neutral conditions in satisfactory yields. Sydnones (1) are archetypal members of the class of compounds known as mesoionic which were first prepared by Earl and his co-workers in 1935. 1They undergo a variety of transformations including electrophilic aromatic substitution (at the 4-pos… Show more

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Cited by 20 publications
(10 citation statements)
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“…In continuation of our on-going research on various transformations by halogenating agents [26][27][28][29][30][31][32], herein we reported the use of DBH as a more robust and efficient catalyst for the one-pot synthesis of the aryl-14H-dibenzo[a,j] xanthenes derivatives 3a-o by reaction of -naphthol with different aromatic aldehydes in excellent yields (90%-96%) under solvent free conditions (Scheme 1, Table 1). As shown Scheme 1 a) All the isolated products were characterized by their physical properties, by 1 H and 13 C NMR and IR spectra, and by direct comparison with literature data ( [14][15][16], [22][23][24][25]).…”
Section: Resultsmentioning
confidence: 96%
“…In continuation of our on-going research on various transformations by halogenating agents [26][27][28][29][30][31][32], herein we reported the use of DBH as a more robust and efficient catalyst for the one-pot synthesis of the aryl-14H-dibenzo[a,j] xanthenes derivatives 3a-o by reaction of -naphthol with different aromatic aldehydes in excellent yields (90%-96%) under solvent free conditions (Scheme 1, Table 1). As shown Scheme 1 a) All the isolated products were characterized by their physical properties, by 1 H and 13 C NMR and IR spectra, and by direct comparison with literature data ( [14][15][16], [22][23][24][25]).…”
Section: Resultsmentioning
confidence: 96%
“…We also synthesized a series of aromatic aldehydes (Scheme ), and applied them to synthesize new bis‐coumarin derivatives using condensation of these aldehydes and 4‐hydroxycoumarin catalyzed by Fe 3 O 4 @SiO 2 @Im‐bisethylFc [HC 2 O 4 ] nanocatalyst under optimized conditions (Table ) .…”
Section: Resultsmentioning
confidence: 99%
“…and terephthaldehyde (1 equiv. ), 3,3′‐[(4‐formylphenyl)methylene]bis(4‐hydroxy‐2 H ‐chromen‐2‐one) ( 3o ) was obtained in 71% yield. By controlling the molar ratio of 4‐hydroxycoumarin (4 equiv.)…”
Section: Resultsmentioning
confidence: 99%
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“…In continuation with the search for simple non-hazardous methods for the transformations in organic synthesis using halogenating agents [18][19][20][21][22][23][24][25][26] , herein we report a highly versatile and efficient synthesis of 2-aryl-benzimidazoles 3 from o-phenylenediamine, aldehyde and catalytic amounts of 1,3-dibromo 5,5-dimethyl hydantoin (DBH) under solvent-free and microwave conditions in high yields (Scheme 1).…”
Section: Resultsmentioning
confidence: 99%