53175-35-2

Upstream product

• 98-01-1 furfural 
• 2450-71-7 Propargylamine 
• 617-89-0 furan-2-ylmethanamine 
• 106-96-7 propargyl bromide 

Downstream Products

• 1394238-00-6 N-(furan-2-ylmethyl)-5-[(4-methylbenzene)sulfonyl]-N-(prop-2-yn-1-yl)-5H-[1,2,4]triazino[5,6-b]indole-3-carboxamide 
• 1394236-95-3 13-(furan-2-ylmethyl)-8-[(4-methylbenzene)sulfonyl]-8,10,13-triazatetracyclo[7.7.0.02,7.011,15]hexadeca-1⁽¹⁶⁾,2⁽⁷⁾,3,5,9,11⁽¹⁵⁾-hexaen-12-one 
• 317834-58-5 N-(furan-2-ylmethyl)-4-methyl-4-N-prop-2-yn-1-ylbenzenesulfonamide 

Relevant academic research and scientific papers

Direct Reductive Amination of Biobased Furans to N-Substituted Furfurylamines by Engineered Reductive Aminase

Furfurylamines are important building blocks for the synthesis of many pharmacologically active compounds and polymers. In this work, direct reductive amination of biobased furans to N-substituted furfurylamines by reductive aminase from Aspergillus oryzae (AspRedAm) was reported. Besides the reductive aminase activity, AspRedAm also showed a promiscuous, yet low alcohol dehydrogenase activity. The variant W210F proved to be a good catalyst for the synthesis of N-substituted furfurylamines. Furans were transformed to the target products with the conversions up to >99% and selectivities up to >99%. In addition, N-substituted furfurylamines were synthesized in the total turnover number (TTN) up to 3200 on a preparative scale, indicating the applicability of this biocatalytic route in synthetic chemistry. (Figure presented.).

Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones

The reactivity of "furan-ynes"in combination with pyridine and quinoline N-oxides in the presence of a Au(I) catalyst, has been studied, enabling the synthesis of three different heterocyclic scaffolds. Selective access to two out of the three possible products, a dihydropyridinone and a furan enone, has been achieved through the fine-tuning of the reaction conditions. The reactions proceed smoothly at room temperature and open-air, and were further extended to a broad substrate scope, thus affording functionalized dihydropyridinones and pyranones.

Palladium-Catalyzed Carbo-Oxygenation of Propargylic Amines using in Situ Tether Formation

1,2-Amino alcohols and α-aminocarbonyls are frequently found in natural products, drugs, chiral auxiliaries, and catalysts. This work reports a new method for the palladium-catalyzed oxyalkynylation and oxyarylation of propargylic amines. The reaction is perfectly regioselective based on the in situ introduction of a hemiacetal tether derived from trifluoroacetaldehyde. cis-Selective carbo-oxygenation was achieved for terminal alkynes, whereas internal alkynes gave trans-carbo-oxygenation products. The obtained enol ethers could be easily transformed into 1,2-amino alcohols or α-amino ketones using hydrogenation or hydrolysis, respectively.

Synthesis method of 3-ethyl formate-5-t-butyloxycarboryl-furo [2,3-c] pyrrole

The invention relates to a synthesis method of 5-t-butyl-3-ethyl-4 H-furo [2,3-c] pyrrole-3, 5 (6H)-diformate, and mainly solves the technical problem of no suitable industrial synthesis method in the prior art. The synthesis method comprises four steps, first, compound 1 (furfural) and propargylamine are reacted in methanol to form an imide intermediate, the imide intermediate is reduced by sodium borohydride to obtain a compound 2, Boc anhydride is added for overnight reaction at room temperature to obtain a compound 3, the compound 3 and lithium diisopropylamide are reacted to form a lithium salt of the compound 3, ethyl chloroformate is added for reaction to obtain a compound 4, and finally the compound 4 and 3, 6-bis (2-pyridinyl)-1, 2, 4, 5-tetrazine are dissolved in toluene for overnight refluxing by heating to obtain the final target compound.

Bicyclic Guanidine Catalyzed Asymmetric Tandem Isomerization Intramolecular-Diels-Alder Reaction: The First Catalytic Enantioselective Total Synthesis of (+)-alpha-Yohimbine

Hydroisoquinoline derivatives were prepared in moderate to good enantioselectivities via a bicyclic guanidine-catalyzed tandem isomerization intramolecular-Diels-Alder (IMDA) reaction of alkynes. With this synthetic method, the first enantioselective synthesis of (+)-alpha-yohimbine was completed in 9 steps from the IMDA products.

An expeditious and atom-economic synthesis of lead-like, medicinally important 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones

We have developed an expeditious and atom-economic synthesis of lead-like, privileged 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones, which is based on Sonogashira coupling and a two-step condensation with hydrazine hydrate leading to two ring-forming events, with full control over the two elements of diversity present.

An intramolecular inverse electron demand Diels-Alder approach to annulated α-carbolines

Intramolecular inverse electron demand cycloadditions of isatin-derived 1,2,4-triazines with acetylenic dienophiles tethered by amidations or transesterifications proceed in excellent yields to produce lactam- or lactone-fused α-carbolines. Beginning with various isatins and alkynyl dienophiles, a pilot-scale library of eighty-eight α-carbolines was prepared by using this robust methodology for biological evaluation.

Facile entry to 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrazin-6-ones from amines and amino acids

A practical and high-yielding regioselective synthesis of several enantiopure 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]-pyrazin-6-ones is described starting from primary amines and α-amino acid derivatives in a three-step reaction sequence by employing a constrained intramolecular "click" reaction as the key step. The method obviates chromatographic purification of products. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.