3688-57-1

Upstream product

• 2216-75-3 furfural phenylhydrazone 
• 617-90-3 2-furancarbonitrile 
• 62-53-3 aniline 
• 609-38-1 furan-2-carboxylic acid amide 
• 54610-73-0 furan-5-carboxamidine 
• 615-42-9 1,2-Diiodobenzene 

Downstream Products

• 111639-81-7 N-phenyl-N'-phenylcarbamoyl-furan-2-carboxamidine 
• 166985-89-3 N¹-Acetyl-N¹-(2-furyl)-N²-phenylurea 
• 350691-95-1 N¹-Furoyl-N¹-(2-furyl)-N²-phenylurea 
• 102-07-8 bis(diphenyl)urea 
• 350691-90-6 N¹-Proanoyl-N¹-(2-furyl)-N²-phenylurea 
• 3878-19-1 fuberidazole 
• 93-98-1 N-phenyl benzoyl amide 
• 89549-39-3 N-benzoylfuran-2-carboxamide 
• 6833-15-4 4-chlorobenzanilide 

Relevant academic research and scientific papers

Direct Synthesis of 3-Acylindoles through Rhodium(III)-Catalyzed Annulation of N-Phenylamidines with α-Cl Ketones

In the present study, a novel synthetic strategy to directly produce versatile 3-acylindoles through Rh(III)-catalyzed C-H activation and annulation cascade of N-phenylamidines with α-Cl ketones was developed, in which α-Cl ketones serve as unusual one-carbon (sp3) synthons. This strategy features high regioselectivity, efficiency, wide substrate tolerance, and mild reaction conditions, which further underscore its synthetic utility in drug molecule synthesis.

N-Heterocyclic carbene-catalyzed annulation of ynals with amidines: Access to 1,2,6-trisubstituted pyrimidin-4-ones

An N-heterocyclic carbene-catalyzed annulation of ynals and amidines has been reported to construct pyrimidin-4-ones. The protocol features a broad substrate scope and mild conditions. Furthermore, an oxidative strategy to catalytically generate ynal-deri

Vanadium-Catalyzed Oxidative C(CO)-C(CO) Bond Cleavage for C-N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides

A novel vanadium-catalyzed one-pot domino reaction of 1,2-diketones with amidines has been identified that enables their transformation into imides and amides. The reaction proceeds by dual acylation of amidines via oxidative C(CO)-C(CO) bond cleavage of 1,2-diketones to afford N,N′-diaroyl-N-arylbenzamidine intermediates. In the reaction, these intermediates are easily hydrolyzed into imides and amides through vanadium catalysis. This method provides a practical, simple, and mild synthetic approach to access a variety of imides as well as amides in high yields. Moreover, one-step construction of imide and amide bonds with a long-chain alkyl group is an attractive feature of this protocol.

CuI-catalyzed amination of arylhalides with guanidines or amidines: A facile synthesis of 1-H-2-substituted benzimidazoles

(Figure Presented) CuI/L5 (N,N′-dimethylethylenediamine) proves to be an efficient catalyst system for the amination of arylhalides with guanidines. The same catalyst system is then successfully applied to the one-step synthesis of 1-H-2-aminobenzimidazol

The oxidative rearrangement of furan-2-carboximidamides: Preparation and properties of 2-acylaminofurans

Oxidation of furan-2-carboximidamides 8 by (dicarboxyiodo)benzenes gives N1-acyl-N1-(2-furyl)ureas 9 via rearrangement to a carbodiimide. Thermolysis of eleven ureas 9 gave the corresponding 2-acylaminofurans 10, which cannot be made from the free amines owing to their high instability. When oxidation of the corresponding benzo[b]furan derivatives 12 was investigated a new type of product was isolated, in addition to the expected ureas 14, and these were shown to be benzo[4,5]furo[2,3-d]pyrimidine derivatives 15. The mechanism of formation of these products must involve reaction of the carbodiimide intermediate with the amidine precursor and cyclisation of the resulting guanidine derivatives 19. The corresponding tetraphenylguanidine 21 was prepared and underwent thermal cyclisation but the quinazoline derivative formed 23 was shown to occur via an alternative cyclisation mechanism. The structures of cyclisation products 15 and 23 were confirmed by X-ray crystallography. N-(2-Furyl)acetamide 10a readily undergoes cycloaddition reactions with electron-deficient alkynes to give phenols after spontaneous ring opening. Observed regioselectivity is in agreement with the results of AM1 molecular orbital calculations. Reaction of the amide 10a with Lawesson's reagent gave the thioamide 26.

Oxidative rearrangement and cyclisation of N-substituted amidines using iodine(III) reagents and the influence of leaving group on mode of reaction

The products of reaction of N-substituted amidines 5 with hypervalent iodine reagents such as (diacetoxyiodo)benzene (DAIB), bis(trifluoroacetoxy)iodobenzene (BFIB) and [methoxy(tosyloxy)-iodo]benzene (MTIB) are determined by the reagent, the amidine substituents and the reaction temperature. C-Alkyl-N-arylamidines 5a-d cyclise in high yield giving benzimidazoles 6 but C,N-dialkyl- and C,N-diaryl-amidines 5e-l rearrange to give products derived from an intermediate carbodiimide. Use of N2-phenylfuran-2-carboximidamide 5j leads to N-(2-furyl)acetamide 15 in good yield, illustrating a convenient route to stable derivatives of highly unstable 2-aminofuran. The rearrangement of C,N-diarylamidines on reaction with DAIB contrasts with the observed formation of benzimidazole when the same precursors are treated with lead tetraacetate (LTA). Evidence is presented to support the view that the mode of reaction is determined by the nature of the leaving group in an imide intermediate 19: very good leaving groups [e.g. PhI, N2, AgCl and PhSO2O- (aq.)] appear to favour rearrangement whereas poorer leaving groups [e.g. Cl-, Me2S, Me3N and PhSO2O- (non-aq.)] favour cyclo-α-elimination.