- Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex
-
A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.
- Pandey, Pragati,Bera, Jitendra K.
-
p. 9204 - 9207
(2021/09/20)
-
- One-Pot Preparation of Aromatic Amides, 4-Arylthiazoles, and 4-Arylimidazoles from Arenes
-
Simple treatment of arenes with α-bromoacetyl chloride and AlCl3, followed by the reaction with molecular iodine and aq. NH3, thioamides, or amidines gave the corresponding primary aromatic amides, 4-arylthiazoles, or 4-arylimidazoles in good yields, respectively. Aryl α-bromomethyl ketones are the key intermediates in those reactions. Primary aromatic amides were formed from arenes through the reaction of aryl α-bromomethyl ketones with molecular iodine and aq. NH3, and 4-arylthiazoles and 4-arylimidazoles were formed from arenes through the reactions of aryl α-bromomethyl ketones with thioamides and amidines, respectively, in one pot under transition-metal-free conditions.
- Yamamoto, Takahiro,Togo, Hideo
-
p. 4187 - 4196
(2018/08/21)
-
- Tandem synthesis of aromatic amides from styrenes in water
-
An expedient one-pot synthesis of aromatic amides has been reported from styrenes in the presence of N-bromosuccinimide and iodine by using aqueous ammonia in water. The reaction proceeds through the formation of α-bromoketone as an intermediate in the pr
- Sathe, Pratima A.,Karpe, Aniket S.,Parab, Aniket A.,Parade, Babasao S.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
-
supporting information
p. 2820 - 2823
(2018/06/25)
-
- Design and synthesis of diaziridinyl quinone thiadiazole hybrids via nitrile sulfide cycloaddition reaction as a key step
-
A series of novel diaziridinyl quinone thiadiazole hybrids (9a-9j) were synthesized starting from 2-hydroxy-5-methoxybenzoic acid 1 in a 7 step synthetic sequence. The key step in the scheme involves the nitrile sulfide cycloaddition reaction of oxathiazo
- Aitha, Anjaiah,Yennam, Satyanarayana,Behera, Manoranjan,Anireddy, Jaya Shree
-
p. 1507 - 1510
(2016/03/12)
-
- Aminofluorene-Mediated Biomimetic Domino Amination-Oxygenation of Aldehydes to Amides
-
A conceptually novel biomimetic strategy based on a domino amination-oxygenation reaction was developed for direct amidation of aldehydes under metal-free conditions employing molecular oxygen as the oxidant. 9-Aminofluorene derivatives acted as pyridoxamine-5′-phosphate equivalents for efficient, chemoselective, and operationally simple amine-transfer oxygenation reaction. Unprecedented RNH transfer involving secondary amine to produce secondary amides was achieved. In the presence of 18O2, 18O-amide was formed with excellent (95%) isotopic purity.
- Ghosh, Santanu,Jana, Chandan K.
-
supporting information
p. 5788 - 5791
(2016/11/29)
-
- N3 as an efficient reagent for the Schmidt reactions of ketones, arylaldehydes and aromatic carboxylic acids
-
Schmidt reaction of arylaldehydes, ketones and aromatic carboxylic acids using task-specific ionic liquid, [bmim]N3 in the presence of AcOH/H2SO4 proceeds at 50-60 °C within 2-4 h to give the corresponding products. Benzaldehydes containing electron releasing groups afforded to the related benzamide derivatives. Benzonitrile derivatives were formed from the reaction of benzaldehydes containing electron withdrawing groups under these conditions. High yields of the related amides and anilines were obtained from the reaction of a variety of ketones and aromatic carboxylic acids, respectively, utilizing this procedure.
- Valizadeh, Hassan,Gholipour, Hamid,Ahmadi, Mina,Vaghefi, Sevil
-
p. 1287 - 1294
(2014/11/07)
-
- 3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents
-
Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guérin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 μg/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 μM, indicating its better safety profile.
- Yang, Jianzhong,Pi, Weiyi,Xiong, Li,Ang, Wei,Yang, Tao,He, Jun,Liu, Yuanyuan,Chang, Ying,Ye, Weiwei,Wang, Zhenling,Luo, Youfu,Wei, Yuquan
-
p. 1424 - 1427
(2013/03/14)
-
- Nitromethane in polyphosphoric acid- A new reagent for carboxyamidation and carboxylation of activated aromatic compou
-
A new method of carboxyamidation of aromatic compounds based on their reaction with nitromethane in polyphosphoric acid has been developed. Upon the hydrolysis of benzamides during the reaction mixture workup, the corresponding benzoic acids can be obtained. Taylor & Francis Group, LLC.
- Aksenov, Alexander V.,Aksenov, Nicolai A.,Nadein, Oleg N.,Aksenova, Inna V.
-
experimental part
p. 541 - 547
(2011/11/29)
-
- Antibacterial alkoxybenzamide inhibitors of the essential bacterial cell division protein FtsZ
-
3-Methoxybenzamide is a weak inhibitor of the essential bacterial cell division protein FtsZ. Exploration of the structure-activity relationships of 3-methoxybenzamide analogues led to the identification of potent anti-staphylococcal compounds.
- Czaplewski, Lloyd G.,Collins, Ian,Boyd, E. Andrew,Brown, David,East, Stephen P.,Gardiner, Mihaly,Fletcher, Rowena,Haydon, David J.,Henstock, Vincent,Ingram, Peter,Jones, Clare,Noula, Caterina,Kennison, Leanne,Rockley, Chris,Rose, Valerie,Thomaides-Brears, Helena B.,Ure, Rebecca,Whittaker, Mark,Stokes, Neil R.
-
scheme or table
p. 524 - 527
(2011/02/28)
-
- Synthesis Directed Towards Putative Advanced Intermediates in Sarubicin A Biosynthesis
-
3,6-Dihydroxyanthranilamide, 5, and its 5-propyl derivative, 15, were synthesized.The former was found to be very unstable, but the later was stable and could be reversibly oxidized to the analogous quinone. 3,6-Dimethoxyanthranilamide was protected as an
- Gould, Steven J.,Eisenberg, Rodney L.,Hillis, Larry R.
-
p. 7209 - 7218
(2007/10/02)
-