Regioselective nitration of aromatic compounds in an aqueous sodium dodecylsulfate and nitric acid medium

Abstract

An aqueous solution of sodium dodecylsulfate in the presence of dilute nitric acid at room temperature works as a mild medium for the nitration of aromatic compounds with high regioselectivity.

Recent advances in catalysis in micellar media

“…They found that in the presence of anionic SDS micelles (50 mM), the reaction of nitric acid 1 M with phenol as the substrate proceeds smoothly at room temperature within 30 minutes leading exclusively to the p-nitrophenol isomer (Scheme 46). 104 The regioselective reaction can be easily extended to other aromatic electron rich substrates like aniline that do not need -NH 2 protection as well as electron poor aromatic substrates such as the nitro, carboxylic acid, keto and other derivatives all leading to the corresponding nitro compounds in good to excellent yields with high regioselectivity imparted by the electronic properties of the substrate. SDS micelles are known to undergo hydrolysis in acidic media and it is likely that in the presence of HNO 3 1-dodecanol is initially formed liberating HSO 4…”

DNA micelles as nanoreactors: efficient DNA functionalization with hydrophobic organic molecules

“…The reactant molecules experience a significant increase in effective concentration, 36 and can undergo a variety of reactions with enhanced yields [37][38][39][40][41] and often altered regio-and stereoselectivity. [42][43][44] Here, we report a simple DNA micelle-templated method to enhance the reactivity of a range of hydrophobic molecules and polymers with DNA, in aqueous buffer and under mild conditions, with excellent yields, short reaction times, and ready purification and separation of the final products. This method expands the range of DNA-templated reactions, because it allows them to occur in an organic micellar core with increased reactant effective concentration.…”

Xylochemical Synthesis of Cytotoxic 2-Aminophenoxazinone-Type Natural Products Through Oxidative Cross Coupling

“…The 2-aminophenols which should end up as the benzenoid ring in the aminophenoxazinone product were synthesized from wood-derived phenols to close the cycle of sustainable starting materials. Methyl 3-amino-4-hydroxybenzoate ( 7a ) for the synthesis of maroxazinone ( 8a ) can be synthesized from 4-hydroxybenzoic acid − in three simple steps by known methods. , The precursor of chandrananimycin A ( 9 ), 2-aminoresorcinol ( 7b ), is available from resorcinol in two steps, , whereas 2,3-dihydroxyaniline ( 7c ), precursor for aminophenoxazinone 8c , was synthesized from 2,3-dihydroxybenzoic acid ( 10 ) in 28% yield over four steps (Scheme ). …”

“…Methyl 3-amino-4-hydroxybenzoate (7a) for the synthesis of maroxazinone (8a) 21 can be synthesized from 4hydroxybenzoic acid 37−39 in three simple steps by known methods. 40,41 The precursor of chandrananimycin A (9), 25 2-aminoresorcinol (7b), is available from resorcinol 42 in two steps, 30,43 whereas 2,3-dihydroxyaniline (7c), precursor for aminophenoxazinone 8c, 23 was synthesized from 2,3-dihydroxybenzoic acid (10) 44 in 28% yield over four steps (Scheme 3). 45 For the synthesis of exfoliazone (11), viridobrunnine A ( 12) and venezueline E (13), a common precursor was prepared.…”