339221-51-1Relevant academic research and scientific papers
Synthesis of various acylating agents directly from carboxylic acids
Pilathottathil, Fathima,Vineet Kumar, Doppalapudi,Kaliyamoorthy, Alagiri
supporting information, p. 1622 - 1632 (2020/04/27)
A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.
Mo(CO)6 as a Solid CO Source in the Synthesis of Aryl/Heteroaryl Weinreb Amides under Microwave-Enhanced Condition
Ningegowda, Raghu,Bhaskaran, Savitha,Sajith, Ayyiliath M.,Aswathanarayanappa, Chandrashekar,Padusha, M. Syed Ali,Priya, Babu Shubha
, p. 44 - 51 (2017/01/21)
The facile transformation of aryl/heteroaryl nonaflates into corresponding amides via Pd-catalyzed aminocarbonylation using Mo(CO)6 as a solid CO source under microwave-enhanced condition is reported. The method was found to be tolerant with respect to a
One-pot transition-metal-free synthesis of weinreb amides directly from carboxylic acids
Niu, Teng,Wang, Ke-Hu,Huang, Danfeng,Xu, Changming,Su, Yingpeng,Hu, Yulai,Fu, Ying
, p. 320 - 330 (2014/02/14)
Weinreb amides were prepared directly from carboxylic acids, N,O-dimethylhydroxylamine, and phosphorus trichloride in one pot at 60 °C in toluene in high yields, thus avoiding the separation of the moisture and air sensitive intermediate P[NMe(OMe)]3 in advance. Sterically hindered carboxylic acids also give the corresponding Weinreb amides in excellent yields. Various functional groups are tolerated on the carboxylic acid. The method, which is a simple process and gives high yields, is suitable for large-scale production. Georg Thieme Verlag KG Stuttgart · New York.
A Weinreb amide approach to the synthesis of trifluoromethylketones
Rudzinski, Diandra M.,Kelly, Christopher B.,Leadbeater, Nicholas E.
supporting information, p. 9610 - 9612 (2012/10/29)
A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert-Prakash reagent (TMS-CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.
A facile one-pot synthesis of acyclic β-enamino ketones, an important class of versatile synthetic intermediates
Choudhury, Anusuya,Breslav, Michael,Grimm, Jeffrey S.,Xiao, Tong,Xu, Dawei,Sorgi, Kirk L.
, p. 3069 - 3072 (2008/02/02)
A one-pot sequential process consisting of nucleophilic substitution of the lithiated acetylides with Weinreb amides followed by a Michael reaction of the extruded N-methoxy-N-methylamine after quenching with saturated NH4Cl, provided β-enamino ketones in high yield and in a single geometrical isomeric form. It has been demonstrated that this method is applicable to a wide variety of such amides and to different acetylides.
