ZnCl2/PhI=O Mediated Selective ortho-Chlorination of Amides

: A new ortho-chlorination system consisted of zinc(II) and hypervalent iodine(III) reagent was developed for ortho-chlorination of amides, and the desired products were obtained in moderate to good yields (38 - 85%). This highly facile and convenient methodology was tolerant of aromatic amide and alkyl amide with diverse substituted groups. A plausible mechanism was illustrated in which carbocation rearrangement and metal salt coordinate facilitated ortho-chlorination were involved.

Tropylium-Promoted Ritter Reactions

The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuable N-alkyl amide products. However, this reaction has not been frequently...

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 by 1H-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.

N-Alkyl amide synthesis via N-alkylation of amides with alcohols

The present review summarizes the recent development of N-alkylation of amides with alcohols according to the classification of catalysts.

Synthesis, anti-mycobacterial and cytotoxic evaluation of substituted isoindoline-1,3-dione-4-aminoquinolines coupled via alkyl/amide linkers

A series of secondary amine-substituted isoindoline-1,3-dione-4-aminoquinolines were prepared via microwave heating and assayed for their anti-mycobacterial activities.