An efficient deuteration method through the ex situ generation of D₂ for the reductive deuteration of biologically significant α-substituted acrylic acids and enamide derivatives is reported. This method was successfully applied to the synthesis of deuterated analogs of marketed NSAIDs such as ibuprofen, flurbiprofen, and naproxen. Additionally, it facilitates late-stage deuteration of enamides and N-vinylated drugs. Moreover, the method was extended to N-viny azoles, cinnamic acid derivatives, and other unsaturated substrates toward deuteration reaction. This technique utilizes D₂O as a safe and economical deuterium source. Notably, the reaction is performed in a standard fume hood setup, ensuring ease of handling and enhanced practicality.

31 Jan 2025·The Journal of Organic Chemistry

Rapid Synthesis of Primary Amides Using Ammonia Borane

Article

Author: Han, Hui ; Li, Xiao-Yun ; Chen, Xuenian ; Ma, Yan-Na ; Liu, Zhenxing ; Kang, Jia-Xin

We report the rapid synthesis of primary amides by directly using commercially available ammonia borane (NH₃·BH₃), sodium hexamethyldisilazide (NaHMDS), and esters. The success of this protocol relies on NH₃·BH₃ as the nitrogen source being considerably more convenient and NaHMDS being an excellent proton abstractor but not participating in the nucleophilic addition reaction. The reaction had a wide substrate scope containing bioactive molecules, and most of the substrates were efficiently amidated over 90% yields.

01 Jan 2025·Vibrational Spectroscopy

The infrared spectra of primary amides, Part 2. Deuteration of benzamide and hydrogen bonding effects of ortho alkoxybenzamides

Author: Threlfall, T. L. ; Grinter, R. ; Threlfall-Holmes, P. N.

The wavenumber values in the carbonyl and NH₂ stretching regions of a further 21 amides, all ortho substituted benzamides or heterocyclic carboxamides, are presented.The previous limits on the spectral ranges are thereby widened marginally, but in predictable ways.The NH stretching vibrations of ortho alkoxybenzamides are related to benzamide itself by a curve dependent on intramol. hydrogen bonding, quantified by further elaboration of the Linnett equations to account for non-equivalence of the two NH bonds.Deuteration experiments enabled uncoupling of the NH bonds and assignment of bond strengths.Although it is widely believed that there is no coupling between XH and XD stretching frequencies, we show that the true NH frequency is raised by 2 cm^-1 as a result of deuterium coupling in NHD groups.The calculation of ND₂ wavenumbers from those of the fundamental and first overtone of the NH₂ values was carried out by 4 procedures.Better concordance with the antisym. vibration than the sym. vibration was observedThe calculated shortening of the NH bonds on deuteration is 0.0035±0.0009 Å .

100 Deals associated with Ethenzamide

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KEGG	Wiki	ATC	Drug Bank
D01466	Ethenzamide	N02BA07	DB13544

R&D Status

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Indication	Country/Location	Organization	Date
Inflammation	China	Harbin Pharmaceutical Group Co., Ltd.	01 Jul 2003
Fever	Japan	Yoshida Pharmaceutical Co. Ltd.	01 Apr 1988
Pain	Japan	Yoshida Pharmaceutical Co. Ltd.	01 Apr 1988

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