38470-54-1

Upstream product

• 541-57-1 4-hydroxy-2(5H)-furanone 
• 100-46-9 benzylamine 
• 4971-56-6 tetrahydrofuran-2,4-dione 
• 1343468-59-6 methyl 3-benzylamino-5-oxo-2,5-dihydrofuran-2-carboxylate 
• 103930-94-5 dimethyl 3-(benzylamino)pent-2-enedioate 
• 1134834-55-1 C₁₃H₁₆ClNO₂ 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 69556-70-3 4-methoxy-5H-furan-2-one 

Downstream Products

• 784184-69-6 1-benzyl-2-propyl-2,7-dihydro-1H-furo[3,4-b]pyridin-5-one 
• 784184-83-4 4-benzyl-4,4a,5,6,7,8-hexahydro-3H-furo[3,4-b]quinolin-1-one 
• 898568-59-7 1-benzyl-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,7-dihydro-1H-furo[3,4-b]pyridin-5-one 
• 934296-33-0 C₂₁H₂₃NO₂ 

Relevant academic research and scientific papers

Unexpected Knoevenagel self-condensation reaction of tetronic acid: synthesis of a new class of organic heterocyclic salts

A new class of pyridinium, quinolinium, isoquinolinum, and N-methylimidazolium-3-(2,5-dihydro-5-oxofuran-3-yl)-4-hydroxyfuran-2(5H)-one salts have been prepared in high yields by reacting pyridine, quinoline, isoquinoline, N-methylimidazole, 1,4-diazabicyclo[2.2.2]octane, and their derivatives with tetronic acid in CH2Cl2.

Decarboxylative Knoevenagel-type reactions on tetronamides: Synthesis of 5-ylidene-4-amino-2(5 H)-furanones

A detailed account regarding the synthesis of 5-ylidene-2(5H)-furanones is given. The key step is a decarboxylative Knoevenagel-type reaction of tetronamides with various α-functionalized aldehydes. The synthesis of protected basidalin is presented. Georg

N -bromosuccinimide-promoted cyclization of -carboxymethyl enamino esters; Synthesis of functionalized 4-amino-2(5 H)-furanones

An easy, two-step approach to various 5-carboxymethyl-2(5H)-furanones is described. A detailed study of the reaction of -carboxymethyl enamino esters with N-bromosuccinimide is presented. Georg Thieme Verlag Stuttgart - New York.

METHOD FOR PRODUCING 4-AMINOBUT-2-ENOLIDES

The present invention relates to a process for preparing 4-aminobut-2-enolides and also corresponding intermediates and starting compounds which are passed through or used in the process according to the invention.

N-substituted tetronamides as ambident nucleophilic building blocks for the synthesis of new 4-aza-2,3-didehydropodophyllotoxins

Aza-analogues of podophyllotoxin were synthesized in two steps from N-substituted tetronamides. The acid-mediated benzhydrylation of N-substituted tetronamides with a suitably func-tionalized benzhydrol quantitatively afforded the cyclization precursors.

Tetronamides as latent acyclic vinylogous amides in formal Aza-[3 + 3] cycloaddition reactions with α,β-unsaturated iminium salts. An unexpected rearrangement and an approach to synthesis of substituted piperidines

A detailed account regarding formal aza-[3 + 3] cycloaddition reactions of tetronamides with α,β-unsaturated iminium salts is described here. This investigation uncovers regioisomeric cycloadducts that were not found in previous studies involving this for

A Novel and Highly Stereoselective Approach to Aza-Spirocycles. A Short Total Synthesis of 2-epi-(±)-Perhydrohistrionicotoxin and an Unprecedented Decarboxylation of 2-Pyrones

(Matrix Presented) A novel and highly stereoselective synthesis of aza-spirocycles is described. An application of this methodology is illustrated as a short and concise total synthesis of 2-epi-(±)-perhydrohistrionicotoxin with high diastereomeric contro

Heterocycle Formation through Aza-Annulation: Stereochemically Controlled Syntheses of (+/-)-5-Epitashiromine and (+/-)-Tashiromine

N-alkenylamines, stabilized through conjugation with an electron-withdrawing group, undergo aza-annulation with acryloyl chloride to provide a convergent route for the construction of six-membered nitrogen heterocycles.In addition to enhancing the C-alkylation process of annulation relative to the competing N-acylation process, the electron withdrawing substituent controlled the regioselectivity of alkene formation in both the intermediate enamine and in the unsaturated lactam product.A variety of functional groups, which include -COMe, -COPh, -CO2R, -CONHPh, -CN, -P(O)(OEt)2, and -SO2Ph, were used to determine the effect of the electron-withdrawing substituents upon both the annulation reaction with acryloyl chloride and the subsequent hydrogenation process.When the enamide annulation product was stabilized through conjugation with ester or amide substituents, catalytic hydrogenation of the aza-annulation product resulted in the formation of vicinal stereocenters with high cis selectivity.The utility of this methodology was demonstrated by application of the condensation/aza-annulation/hydrogenation sequence as the key for construction and stereochemical control of the indolizidine ring system of (+/-)-tashiromine.

Construction of Hydroxylated Alkaloids (+/-)-Mannonolactam, (+/-)-Deoxymannojirimycin, and (+/-)-Prosopinine through Aza-Annulation

The aza-annulation of β-enamino carbonyl substrates with acrylate derivatives provides an efficient and convenient route for the regioselective construction of δ-lactams.This two-step ring-forming sequence involved initial generation of the benzyl enamine through either a condensation or conjugate addition reaction with BnNH2, followed by aza-annulation with acryloyl chloride or acrylic anhydride.Controlled by the rigid framework of the intermediate lactam, introduction of ring substituents was accomplished with high relative stereoselectivity.The carbonyl functionality, which was necessary to direct the regioselectivity of the aza-annulation reaction, was then transformed into a protected hydroxyl substituent through Baeyer-Villiger oxidation.The resultant δ-lactam product was used as a valuable intermediate in the synthesis of three natural products.Subsequent modification of this δ-lactam gave the naturally occurring α-mannosidase inhibitors (+/-)-mannonolactam and (+/-)-deoxymannojirimycin, while synthesis of the alkaloid (+/-)-prosopinine was accomplished through homologation of the lactam carbonyl.

2(3H)- AND 2(5H)-FURANONES. III. AN EFFICIENT SYNTHESIS AND THE ESCHENMOSER-MANNICH REACTION OF N-SUBSTITUTED 4-AMINO-2(5H)-FURANONE

A series of N-substituted 4-amino-2(5H)-furanones (II) was derived from β-tetronic acid (I) by direct action of several aliphatic and aromatic amines.The Eschenmoser-Mannich reaction of II readily gave the corresponding Mannich bases (VI) quantitatively.