90009-47-5

Upstream product

• 64-17-5 ethanol 
• 555-59-9 N-phenylmaleamic acid 
• 62-53-3 aniline 
• 941-69-5 N-phenyl-maleimide 
• 115-11-7 isobutene 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 105-58-8 Diethyl carbonate 
• 64-67-5 diethyl sulfate 

Downstream Products

• 941-69-5 N-phenyl-maleimide 
• 17722-43-9 ethyl 4-oxo-4-(phenylamino)butanoate 

Relevant academic research and scientific papers

Iron(III) Chloride/Phenylsilane-Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly-Substituted γ-Butyrolactones

A iron-catalyzed free radical cascade reaction of allyl alcohols with N-substituted maleimides for accessing poly-substituted γ-butyrolactones has been developed. In this protocol, various allyl alcohols can open N-substituted maleimide rings to form allyl ester intermediates, and the allyl ester intermediates can be converted into an allyl ester alkyl radicals and undergo intramolecular free radical addition cyclization to form a polysubstituted γ-butyrolactones. In this protocol, spiro γ-butyrolactone compounds can be also synthesized. Meanwhile, the strategy could be applied to further construct a fully substituted tetrahydrofuran. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. (Figure presented.).

An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters

Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOCl2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC. HCl and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOCl 2 at 0-5°C give the monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group of the ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.

A facile and green synthesis of N-substituted imides

Anhydrides 1, 6 and 10 have been reacted, independently, with aromatic primary amines 2 in solid phase by simple physical grinding of reactants with p-toluenesulphonicacid as a catalyst to yield corresponding open chain derivatives, monoacid monoamides3,7 and 11 respectively. The latter have each been transformed into the corresponding cyclic derivatives, i.e. imides 5, 9 and 13 respectively in solid phase by simple physical grinding of each with K 2CO3, alkylating agent and tetrabutylammoniumbromide as a catalyst with short reaction times. These cyclic imides can also be obtained by physical grinding of each of 3, 7 and 11 with dicyclohexylcarbodimide as a dehydrating agent in solid phase.

The Synthesis of (3'-Oxo-3',4'-dihydro-2'H-1',4'-benzothiazin-2'-yl)acetic Acid and (3'-Oxo-3',4'-dihydro-2'H-1',4'-benzoxazin-2'-yl)acetic Acid Derivatives

Reaction of o-aminophenol with various maleic anhydrides gave first 2-hydroxymaleanilic acids (4-(2'-hydroxyphenylamino)-4-oxobut-2-enoic acids) (1), which were then converted into the 3-oxo-1,4-benzoxazines (1d-h) and (3f-l) under mild basic conditions:

Esterification of Maleanilic Acids: Intramolecular Esterification Through Imidate Ester

Maleanilic acids are easily esterified at room temperature with an abs. alcohol in the presence of thionyl chloride.It has been shown to proceed through an intramolecular migration of alkyl group of the intermediate imidate ester.

ESTERIFICATION AT ROOM TEMPERATURE: A MIXING AFFAIR ONLY

Carboxylic acids in absolute alcohols, on treatment with thionyl chloride at room temperature give good yields of corresponding esters.