33054-04-5Relevant academic research and scientific papers
Synthesis of: N -methylated amines from acyl azides using methanol
Chakrabarti, Kaushik,Dutta, Kuheli,Kundu, Sabuj
supporting information, p. 5891 - 5896 (2020/08/21)
The transformation of acyl azide derivatives into N-methylamines was developed using methanol as the C1 source via the one-pot Curtius rearrangement and borrowing hydrogen methodology. Following this protocol, various functionalised N-methylated amines were synthesized using the (NNN)Ru(ii) complex from carboxylic acids via an acyl azide intermediate. Several kinetic studies and DFT calculations were carried out to support the mechanism and also to determine the role of the Ru(ii) complex and base in this transformation.
Direct conversion of carboxylic acids to various nitrogen-containing compounds in the one-pot exploiting curtius rearrangement
Kumar, Arun,Kumar, Naveen,Sharma, Ritika,Bhargava, Gaurav,Mahajan, Dinesh
, p. 11323 - 11334 (2019/09/10)
Herein we report, a single-pot multistep conversion of inactivated carboxylic acids to various N-containing compounds using a common synthetic methodology. The developed methodology rendered the use of carboxylic acids as a direct surrogate of primary amines, for the synthesis of primary ureas, secondary/tertiary ureas, O/S-carbamates, benzoyl ureas, amides, and N-formyls, exploiting the Curtius reaction. This approach has a potential to provide a diversified library of N-containing compounds, starting from a single carboxylic acid, based on the selection of the nucleophile.
Palladium-Catalyzed One-Pot Synthesis of N -Sulfonyl, N -Phosphoryl, and N -Acyl Guanidines
Qiao, Guanyu,Zhang, Zhen,Huang, Baoliang,Zhu, Liu,Xiao, Fan,Zhang, Zhenhua
supporting information, p. 330 - 340 (2018/01/12)
An efficient palladium-catalyzed cascade reaction of azides with isonitrile and amines is presented; it offers an alternative facile approach toward N -sulfonyl-, N -phosphoryl-, and N -acyl-functionalized guanidines in excellent yield. These series of substituted guanidines exhibit potential biological and pharmacological activities. In addition, the less reactive intermediate benzoyl carbodiimide could be isolated by silica gel column flash chromatography in moderate yield.
Design and synthesis of uracil urea derivatives as potent and selective fatty acid amide hydrolase inhibitors
Qiu, Yan,Ren, Jie,Ke, Hongwei,Zhang, Yang,Gao, Qi,Yang, Longhe,Lu, Canzhong,Li, Yuhang
, p. 22699 - 22705 (2017/07/10)
Fatty acid amide hydrolase (FAAH) is one of the key enzymes involved in the biological degradation of endocannabinoids, especially anandamide. Pharmacological blockage of FAAH restores the levels of endocannabinoids, providing therapeutic benefits in the management of inflammation, depression and multiple sclerosis. In this study, a series of uracil urea derivatives as FAAH inhibitors were designed and synthesized. Structural modifications at the C5 position and side chain of N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide (1a) led to FAAH inhibitors with improved potency and selectivity. Structure-activity relationship (SAR) studies indicated that C5 electron-withdrawing substituents were preferred for optimal potency but not for selectivity, whereas replacement of the alkyl chain with phenylalkyl moieties or biphenyl groups significantly improved both inhibitory potency and selectivity towards FAAH. Two highly potent picomolar FAAH inhibitors (4c, IC50 = 0.3 ± 0.05 nM; 4d, IC50 = 0.8 ± 0.1 nM) were developed. Compound 4c inhibited FAAH in a rapid, selective, noncompetitive, and irreversible pattern. This study provides several highly potent and selective FAAH inhibitors and an optimized chemical scaffold for the development of FAAH inhibitors. We anticipate that these FAAH inhibitors will enable new possibilities in understanding FAAH functions and development of therapeutics for pain and inflammatory diseases.
Visible light C-H amidation of heteroarenes with benzoyl azides
Brachet,Ghosh,Ghosh,K?nig
supporting information, p. 987 - 992 (2015/02/19)
Benzoyl azides were used for the direct and atom economic C-H amidation of electron rich heteroarenes in the presence of phosphoric acid, a photocatalyst and visible light. Hetero-aromatic amides are obtained in good yields at very mild reaction conditions with dinitrogen as the only by-product. The reaction allows the use of aryl-, heteroaryl- or alkenyl acyl azides and has a wide scope for heteroarenes, including pyrroles, indole, furan, benzofuran and thiophene giving good regio-selectivities and yields.
Direct and facile synthesis of acyl azides from carboxylic acids using the trichloroisocyanuric acid-triphenylphosphine system
Akhlaghinia, Batool,Rouhi-Saadabad, Hamed
, p. 181 - 185 (2013/05/09)
A mild, efficient, and practical method for the one-step synthesis of acyl azides from carboxylic acids using a safe and inexpensive mixed reagent, trichloroisocyanuric acid-triphenylphosphine, is described.
Copper-mediated amidation of alkenylzirconocenes with acyl azides: Formation of enamides
Liu, Hailan,Zhou, Yiqing,Yan, Xiaoyu,Chen, Chao,Liu, Qingbin,Xi, Chanjuan
supporting information, p. 5174 - 5177 (2013/11/06)
Copper-mediated amidation of alkenylzirconocenes generated in situ from alkynes and zirconocenes with acyl azides is accomplished under mild conditions. The reaction can be used to prepare various enamides.
One-pot, direct synthesis of acyl azides from carboxylic acids using Ph2PCl/I2/NaN3 reagent system
Nowrouzi, Najmeh,Zareh Jonaghani, Mohammad
, p. 442 - 445 (2012/05/20)
A mild, efficient and simple method for the preparation of acyl azides from carboxylic acids using chlorodiphenylphosphine in the presence of molecular iodine and sodium azide is described.
Application of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) for the synthesis of acid azides
Naik, Shankar A.,Lalithamba,Sureshbabu, Vommina V.
scheme or table, p. 103 - 109 (2011/04/15)
Conversion of acids to acyl azides using peptide coupling agent TBTU has been demonstrated. The procedure is simple and applicable to a range of carboxylic acids under mild reaction conditions. The protocol is extended to the synthesis of urethane protect
