73286-67-6

Upstream product

• 2658-24-4 2,2-dimethylaziridine 
• 108-22-5 Isopropenyl acetate 
• 108-24-7 acetic anhydride 
• 2878-14-0 2-methylallylamin 
• 64-19-7 acetic acid 
• 28148-54-1 2-methylallylamine hydrochloride 
• 18292-38-1 2-methallyltrimethylsilane 
• 75-05-8 acetonitrile 
• 21392-66-5 1-(acetyl)-2,2-dimethylaziridine 

Downstream Products

• 113261-14-6 N-(2-hydroxy-2-methyl-3-phenylthiopropyl)acetamide 
• 113261-13-5 2,5-dimethyl-5-phenylthiomethyl-4,5-dihydro-1,3-oxazole 
• 133523-81-6 2,5-Dimethyl-5-phenylselanylmethyl-4,5-dihydro-oxazole 

Relevant academic research and scientific papers

New lead discovery of herbicide safener for metolachlor based on a scaffold-hopping strategy

The use of herbicide safeners can significantly alleviate herbicide injury to protect crop plants and expand the application scope of the existing herbicides in the field. Sanshools, which are well known as spices, are N-alkyl substituted compounds extracted from the Zanthoxylum species and have several essential physiological and pharmacological functions. Sanshools display excellent safener activity for the herbicide metolachlor in rice seedlings. However, the high cost of sanshools extraction and difficulties in the synthesis of their complicated chemical structures limit their utilization in agricultural fields. Thus, the present study designed and synthesized various N-alkyl amide derivatives via the scaffold-hopping strategy to solve the challenge of complicated structures and find novel potential safeners for the herbicide metolachlor. In total, 33 N-alkyl amide derivatives (2a–k, 3a–k, and 4a–k) were synthesized using amines and saturated and unsaturated fatty acids as starting materials through acylation and condensation. The identity of all the target compounds was well confirmed by1H-NMR,13C-NMR, and high-resolution mass spectrometry (HRMS). The primary evaluation of safener activities for the compounds by the agar method indicated that most of the target compounds could protect rice seedlings from injury caused by metolachlor. Notably, compounds 2k and 4k displayed excellent herbicide safener activities on plant height and demonstrated relatively similar activities to the commercialized compound dichlormid. Moreover, we showed that compounds 2k and 4k had higher glutathione S-transferase (GST), superoxide dismutase (SOD), catalase (CAT), peroxidase (POD), and polyphenol oxidase (PPO) activities in rice seedlings, compared to the metolachlor treatment. In particular, 2k and 4k are safer for aquatic organisms than dichlormid. Results from the current work exhibit that compounds 2k and 4k have excellent crop safener activities toward rice and can, thus, be promising candidates for further structural optimization in rice protection.

Additive-free chemoselective acylation of amines

Aliphatic and aromatic amines are efficiently acylated by acetic, pivalic, benzoic, phthalic, or maleic anhydrides in ethyl acetate at room temperature. Under the same experimental conditions, amino alcohols are chemoselectively acylated at the amino group.

Organoselenium- and Proton-Mediated Cyclization Reactions of Allylic Amides and Thioamides. Syntheses of 2-Oxazolines and 2-Thiazolines

A variety of allylic amides and thioamides were treated with phenylselenenyl bromide in chloroform to give, via 5-exo cyclization, 2-oxazolines and 2-thiazolines, respectively, carrying a (phenylselenenyl)methyl substituent in the 5-position.In some cases (N-crotyl- and N-cinnamylamides/thioamides), dihydro-1,3-oxazines/-thiazines were formed via 6-endo cyclization.The phenylselenenyl group of the cyclofunctionalization products was slowly eliminated by treatment with m-chloroperbenzoic acid to introduce unsaturation in the resulting oxazoline/thiazoline.Reductive removal of the phenylselenenyl group was effected by treatment with triphenyltin hydride.This reaction was sometimes accompanied by a rearrangement of the heterocyclic ring.Proton-induced cyclizations of allylic thioamides to give 2-thiazolines was slowly but efficiently effected in boiling toluene containing a catalytic amount of p-toluenesulfonic acid.

New Routes to Heterocycles via Sulphenylation of Unsaturated Amides

The reaction of manganese(III) acetate with diphenyl disulphide in dichloromethane-trifluoroacetic acid in the presence of N-allylacetamide, followed by hydrolysis, affords a vicinal hydroxy sulphide.Similarly, addition to N-allyltrifluoroacetamide affords hydroxy sulphide adducts, but with different regioselectivity.N-Allylbenzamide and other unsaturated benzamides under similar conditions give cyclic products, 4,5-dihydro-1,3-oxazoles.Homoallylic amides give 5,6-dihydro-4H-1,3-oxazines.Amides derived from pent-4-enylamine give substituted pyrrolidines by cyclisation through nitrogen, but N-hex-5-enylbenzamide gives only an acyclic adduct.Unsaturated carboxylic acids and unsaturated carboxamides are transformed in good yield into lactones under similar conditions.

New Allylation Reaction using Allylmetal (Group IVb) Compounds: Synthesis of N-Allylamides

Reaction of allylsilanes 1a and 1d or allylstannane 1b with thallium(III) salts in nitriles such as acetonitrile, acrylonitrile, propionitrile, and benzonitrile afforded the corresponding N-allylamides.Thus, umpolung of reactivity of allylsilane and allylstannane has been established.Keywords-umpolung of reactivity; allylsilane; allylstannane; N-allylamide; thallium(III) salt; nitrile

Isomerization of N-Allylamides and -imides to Aliphatic Enamides by Iron, Rhodium, and Ruthenium Complexes

Substituted aliphatic N-propenylamides and -imides are readily sythesized from N-allylamides by double bond migration induced by rhodium or ruthenium hydrides.N-Propenylimides can be prepared from allylimides only in the presence of iron pentacarbonyl.