2144-17-4

Upstream product

• 6937-52-6 N,N-diisopropyl-4-methylbenzamide 
• 874-60-2 4-methyl-benzoyl chloride 
• 75-31-0 isopropylamine 
• 19172-47-5 Lawessons reagent 
• 50684-43-0 4-methylbenzothioic S-acid 
• 99-94-5 p-Toluic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 67-63-0 isopropyl alcohol 
• 64-18-6 formic acid 
• 624-31-7 4-tolyl iodide 
• 693-13-0 diisopropyl-carbodiimide 
• 88229-12-3 N-cyclopropyl-4-methylbenzamide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 874-58-8 4-methylbenzoyl bromide 

Downstream Products

• 99-94-5 p-Toluic acid 
• 75-31-0 isopropylamine 
• 85046-77-1 C₁₃H₁₄N₂O₃ 
• 104-85-8 para-methylbenzonitrile 
• 1433955-34-0 2-isopropyl-6-methyl-3,4,7,8,9,10-hexaphenylbenzo[h]isoquinolin-1(2H)-one 
• 1433955-39-5 2-isopropyl-6-methyl-3,4,7,8,9,10-hexa-(4-butylphenyl)benzo[h]isoquinolin-1(2H)-one 
• 70894-75-6 N-(4-methylbenzyl)propan-2-amine 
• 80275-06-5 2,3,6,7-tetrahydro-3-isopropyl-2-(4-methylphenyl)-cyclopenta[e][1,3]oxazin-4(5H)-one 

Relevant academic research and scientific papers

σ-Bond Hydroboration of Cyclopropanes

Hydroboration of alkenes is a classical reaction in organic synthesis in which alkenes react with boranes to give alkylboranes with subsequent oxidation resulting in alcohols. The double bond (π-bond) of alkenes can be readily reacted with boranes owing to its high reactivity. However, the single bond (σ-bond) of alkanes has never been reacted. To pursue the development of σ-bond cleavage, we selected cyclopropanes as model substrates since they present a relatively weak σ-bond. Herein, we describe an iridium-catalyzed hydroboration of cyclopropanes, resulting in β-methyl alkylboronates. These unusually branched boronates can be derivatized by oxidation or cross-coupling chemistry, accessing "designer"products that are desired by practitioners of natural product synthesis and medicinal chemistry. Furthermore, mechanistic investigations and theoretical studies revealed the enabling role of the catalyst.

Chemoselective Synthesis of α-Amino-α-cyanophosphonates by Reductive Gem-Cyanation-Phosphonylation of Secondary Amides

A novel approach to α-amino-α-cyanophosphonates has been developed. The method features a Tf2O-mediated reductive geminal cyanation/phosphonylation of secondary amides. Mild reaction conditions, high bond-forming efficiency, inexpensive readily available starting materials, and good to excellent yields with wide functional group compatibility constitute the main advantages of this method. The protocol can be run on a gram scale.

Introduction of Z-GP scaffold into procarbazine reduces spermatoxicity and myelosuppression

Incorporation of carbobenzoxy-glycylprolyl (Z-GP) to either α or β position of the hydrazine moiety in procarbazine (Pcb) has been carried on in 5-steps process. The overall yield was 32.7%. The new entity Z-GP-Pcb was confirmed targeting to fibroblast activation protein-α (FAPα). Z-GP-Pcb may be hydrolyzed by either isolated rhFAPα or tumor homogenate. It was shown far less cytotoxicity against NCI-H460 cell line than Pcb. Z-GP-Pcb was displayed the potency to reduce spermatoxcity in H22-bearing mice. The mechanism may be ascribed to the blockade of dehydrogenation by α-glycerolphosphate dehydrogenase. This candidate was further proved equal antitumor activity to Pcb. However, the introduction of Z-GP scaffold decreased myelosuppression. All the evidences support that Z-GP-Pcb is a better antitumor agent than Pcb.

Synthesis process of anti-cancer medicine propiconazole (by machine translation)

The synthesis method has the advantages of reasonable design, simplified synthesis method, high unit reaction yield, mild conditions, reduced energy consumption and resource conservation, thereby effectively 4 - solving the problems and disadvantages in the existing device 136 mg 1.0 mmol 10 ml 3.0 ml 80 °C 3 h. (by machine translation)

Synthetic method of procarbazine

The invention discloses a synthetic method of procarbazine (Pcb). The synthetic method comprises following steps: p-tolualdehyde is taken as an initial raw material, dibromocyanuric acid and isopropylamine are added, reaction is carried out at room temperature so as to obtain p-methyl benzoyl isopropylamine; p-methyl benzoyl isopropylamine is dissolved in an organic reagent, N-bromo-succinimide and an initiator are added, heating reflux is carried out, after reaction, the solvent is removed, acetonitrile and a hydrolysis promoter are added, heating reflux is carried out so as to obtain p-formyl benzoyl isopropylamine; p-formyl benzoyl isopropylamine and methylhydrazine sulfate are dissolved in an organic reagent, triethylamine is added for reaction, and the solvent is subjected to rotary drying, sodium cyanoborohydride is added, an obtained reaction system is heated to room temperature, reaction is carried out for more than one night so as to obtain Pcb. According to the synthetic method, bromination is carried out firstly, and then hydrolysis is carried out, p-methyl benzoyl isopropylamine is converted into p-formyl benzoyl isopropylamine, using of strong oxidizing agent and strong acid is avoided, the synthetic method is friendly to the environment, the yield is high, and the total yield of the three steps is 52.9%.

Convenient metal-free direct oxidative amidation of aldehyde using dibromoisocyanuric acid under mild conditions

A facile method for the direct synthesis of amides from aldehydes is described. Amide bonds were synthesized by an oxidative amidation in the presence of dibromoisocyanuric acid (DBI). Treatment of aromatic and aliphatic aldehydes with dibromoisocyanuric acid generated acyl bromide intermediates, which were employed to react with a variety of secondary and primary amines to give amides. Through this reaction method, various amides were synthesized directly from aldehydes under mild conditions in high yields and short times. This facile and efficient procedure provides potential strategy for the direct synthesis of amides from aldehydes.

Towards a Sequential One-Pot Preparation of 1,2,3-Benzotriazin-4(3H)-ones Employing a Key Cp*Co(III)-catalyzed C?H Amidation Step

1,2,3-benzotriazin-4(3H)-one derivatives have been recognised for their potential application as pesticides and pharmaceuticals and new methodologies for their preparation, starting from readily accessible reagents would therefore be an attractive proposition. A wide range of differently substituted benzamides are readily available, which provide an excellent substrate scaffold for the application of direct C?H functionalization protocols. In this context, herein we report the use of a Cp*Co(III) catalyst for the amidation of these benzamides, using 1,4,2-dioxazol-5-ones as amidating agent. The isolable intermediate 2-acetamido benzamide products can thereafter be converted to the desired 1,2,3-benzotriazin-4(3H)-one derivatives through the use of tert-butyl nitrite under mild conditions. It was found to be possible to perform the second step with the crude reaction mixture obtained from the initial C?H amidation step, leading to the overall development of a facile one-pot procedure for the preparation of a range of substituted 1,2,3-benzotriazin-4(3H)-one derivatives, requiring only 5 hours of reaction time, which is also applicable on a gram scale. In addition, the key Cp*Co(III)-catalyzed C?H amidation step has been studied by DFT calculations in order to fully elucidate the mechanism. (Figure presented.).

Synthesis of Amides and Phthalimides via a Palladium Catalyzed Aminocarbonylation of Aryl Halides with Formic Acid and Carbodiimides

A novel method for the preparation of amides and phthalimides has been developed. The process involves a palladium catalyzed aminocarbonylation of an aryl halide, using a carbodiimide and formic acid as the carbonyl source. Experimental data suggest that the mechanistic pathway for this process involves in-situ generation of carbon monoxide from the reaction of formic acid with a carbodiimide in the presence of a palladium catalyst. The method can be used to produce a variety of amides and N-substituted phthalimides efficiently.

TfOH catalyzed One-Pot Schmidt–Ritter reaction for the synthesis of amides through N-acylimides

A One-Pot tandem Schmidt–Ritter process for the synthesis of amides has been developed using the super acid as catalyst. The in situ generated aryl/aliphatic nitriles from the reaction of aldehydes and sodium azide in the presence of TfOH and AcOH (Schmidt reaction) react with suitable alcohol (Ritter reaction) to give the amides. For the first time we observed that during the Schmidt process N-acylimides were generated along with nitriles, interestingly these N-acylimides also participated in the Ritter reaction.

Design of novel CSA analogues as potential safeners and fungicides

Study of safeners has been seldom reported in literature. In this work, a series of novel acylsulfamoylbenzamide analogues was designed and synthesized with newly developed safener cyprosulfamide (CSA) as the leading compound. The activity assay against the herbicide thiencarbazone-methyl (TCM) on maize revealed that fifteen compounds showed better protective effect than CSA on the fresh weight of aerial parts, twelve compounds exhibited better activity on the dry weight of aerial parts. Remarkably, two compounds (6Ih, 7II) had protective effect on the four aspects of TCM treated maize. Further antifungal assay showed their excellent activity against Physollospora piricola. The structure-activity relationships of CSA analogues as safeners and fungicides were discussed and it might be valuable for further molecular modification of new CSA analogues.