1986-61-4

Upstream product

• 100-47-0 benzonitrile 
• 100-01-6 4-nitro-aniline 
• 30924-69-7 N-(4-nitro-benzenesulfonyl)-benzamidine 
• 785-81-9 4-nitro-N-(phenylmethylene)benzenamine 
• 14212-87-4 1,1-bis(N-morpholinyl)ethylene 
• 61253-72-3 C₁₃H₁₀ClN₃O₂ 
• 636-98-6 p-nitrobenzene iodide 
• 1670-14-0 benzamidine monohydrochloride 
• 618-39-3 benzamidin 
• 34918-79-1 N-(4-nitro-phenyl)-benzimidoyl chloride 

Downstream Products

• 61253-72-3 C₁₃H₁₀ClN₃O₂ 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 89060-64-0 1,5-diphenyl-3-methoxycarbonal-1,2,4-triazole 
• 74668-98-7 3-(4-Nitro-phenyl)-2-phenyl-5-(phenyl-hydrazono)-3,5-dihydro-imidazol-4-one 
• 100-01-6 4-nitro-aniline 
• 1449612-17-2 N′-(4-nitrophenyl)-N-(1,2,2-tricyanovinyl)benzamidine 
• 1449576-64-0 2-[5-imino-1-(4-nitrophenyl)-2-phenyl-1H-imidazol-4(5H)-ylidene]malononitrile 
• 89069-73-8 3-(4-nitrophenyl)-2-phenyl-4(3H)-pyrimidinone 
• 89646-95-7 (4R,5R)-1-(4-Nitro-phenyl)-2,5-diphenyl-4,5-dihydro-1H-imidazol-4-ol 
• 89646-91-3 4-[1-(4-Nitro-phenyl)-2,5-diphenyl-4,5-dihydro-1H-imidazol-4-yl]-morpholine 

Relevant academic research and scientific papers

Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate

A new strategy is developed for the synthesis of 1-aminoisoquinoline derivatives. This Rh(III)-catalyzed [4 + 2] annulation reaction employs benzamidines as efficient directing groups and the vinylene carbonate as an acetylene surrogate. Additionally, the reaction features broad substrate scopes and good yields, only producing carbonate anion as byproduct.

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.

Synthesis and structure of aroylamidines and N-arylbenzamidines hydrochlorides

Aroylamidines can be obtained as salts in a reaction of the corresponding arylcarbonitriles with anhydrous ethanol in the presence of dry HCl followed by treating intermediate imidoesters with alcoholic solution of ammonia. N-Arylbenzamidines are obtained by reacting benzonitrile with arylamines in the presence of AlCl3. The structure of arylamines and the reaction conditions signifi cantly affect the yield of the target product, and sometimes the very possibility of its preparation. Pleiades Publishing, Ltd., 2012.

Application of the copper catalysed N-arylation of amidines in the synthesis of analogues of the chemical tool, blebbistatin

A robust protocol for the CuI-catalysed arylation of amidines is presented. Whilst the initially identified conditions were useful for benzamidine-derived substrates, difficulties were encountered with more complex substrates. This problem was overcome following a change in ligand type, enabling the synthesis of analogues of the chemical tool, blebbistatin.

Reinvestigating the synthesis of N-arylbenzamidines from benzonitriles and anilines in the presence of AlCl3

The preparation of N-phenylbenzamidine 3a from the reaction between benzonitrile Ia and aniline in the presence of AId3 is reinvestigated with respect to mode of reagent addition, reaction temperature and Lewis acid catalysis. Pre-forming the nitrile-Lewis acid complex prior to the addition of aniline allows for milder reaction conditions, allowing for the higher yielding synthesis of N-phenylbenzamidine 3a (83%). Using these modified conditions several N-(4-substituted phenyl)benzamidines can be prepared including the N-(4-methoxyphenyl)benzamidine 3b (93%) and the previously unobtainable 2-amino-N-(4-methoxyphenyl)benzamidine 31(56%). All new compounds are fully characterised.

AMIDINE DERIVATIVES WITH NITRIC OXIDE SYNTHETASE ACTIVITIES

Amidine derivative compounds of formula I as defined in the Specification having nitric oxide synthetase inhibitory activity as well as processes for the preparation of and compositions containing said compounds are described

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.

N-haloamidines. VII(2c). 4-Amino-5-chloroimidazoles and 4-amino-5- unsubstituted imidazoles from N-chloro-N'-arylbenzamidines and 1,1- diaminoethenes

N-chloro-N'-arylbenzamidines react with 1,1-diaminoethenes to give in good yields 4-amino-5-chloroimidazoles. The behaviour of these compounds in some nucleophilic substitution reactions and their reduction to 4-amino 5- unsubstituted imidazoles is reported.

Reaction of Sulphuryl Chloride with Some Schiff Bases

The reaction of sulphuryl chloride with schiff bases has been studied.In each case, pure crystalline products have been isolated, and their structures elucidated on the basis of IR, PMR and mass spectral data.A plausible mechanism is advanced for the formation of observed products.