scholarly journals Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

2021 ◽  
Author(s):  
William D. G. Brittain ◽  
Steven L. Cobb
2020 ◽  
Vol 7 (1) ◽  
pp. 50-59
Author(s):  
Kantharaju Kamanna ◽  
S.Y. Khatavi ◽  
P.B. Hiremath

Background: Amide bond plays a key role in medicinal chemistry, and the analysis of bioactive molecular database revealed that the carboxamide group appears in more than 25% of the existing database drugs. Typically amide bonds are formed from the union of carboxylic acid and amine; however, the product formation does not occur spontaneously. Several synthetic methods have been reported for amide bond formation in literature. Present work demonstrated simple and eco-friendly amide bond formation using carboxylic acid and primary amines through in situ generation of O-acylurea. The reaction was found to be more efficient, faster reaction rate; simple work-up gave pure compound isolation in moderate to excellent yield using microwave irradiation as compared to conventional heating. Methods: Developed one-pot synthesis of amide compounds using agro-waste derived greener catalyst under microwave irradiation. Results: Twenty amide bond containing organic compounds are synthesized from carboxylic acid with primary amine catalyzed by agro-waste derived medium under microwave irradiation. First, the reaction involved carboxylic acid activation using EDC.HCl, which is the required base for the neutralization and coupling. The method employed natural agro-waste derived from banana peel ash (WEB) for the coupling gave target amide product without the use of an external organic or inorganic base. Conclusion: In the present work, we demonstrated that agro-waste extract is an alternative greener catalytic medium for the condensation of organic carboxylic acid and primary amine under microwave irradiation. The method found several advantages compared to reported methods like solventfree, non-toxic, cheaper catalyst, and simple reaction condition. The final isolated product achieved chromatographically pure by simple recrystallization and did not require further purification.


CCS Chemistry ◽  
2020 ◽  
pp. 2764-2771
Author(s):  
Bao-Gui Cai ◽  
Shuai-Shuai Luo ◽  
Lin Li ◽  
Lei Li ◽  
Jun Xuan ◽  
...  

2021 ◽  
Author(s):  
Max Lubberink ◽  
Christian Schnepel ◽  
Christopher Baldwin ◽  
Nicholas Turner ◽  
Sabine Flitsch

N-alkanoyl-N-methylglucamides (MEGAs) are non-toxic surfactants widely used in pharmaceutical and biochemical applications and hence more sustainable syntheses towards these compounds are highly desired. Here we present an aqueous, enzymatic synthesis route towards MEGAs and analogues using carboxylic acid reductase (CAR), which has been engineered to catalyse amide bond formation (CAR-A). Compared to lipase catalysed reactions, this biocatalyst is capable of selective amide bond formation between amino-polyols and fatty acids without the competing esterification reaction being observed. The wide substrate scope of CAR-A catalysed amidation was exemplified by the synthesis of 16 amides including several commercially relevant targets. The ATP co-factor could be recycled from cheap polyphosphate using a kinase. This work establishes acyl-phosphate mediated chemistry as a selective strategy for biocatalytic amide bond formation in the presence of competing alcohol functionalities.


Synlett ◽  
2019 ◽  
Vol 30 (15) ◽  
pp. 1795-1798
Author(s):  
Ata Makarem ◽  
Mohammadreza Kamali Sarvestani ◽  
Karel D. Klika ◽  
Klaus Kopka

Bifunctional HBED chelators are hexadentate complexing ligands (chelators) that tightly coordinate to trivalent gallium and, additionally, are able to bind to bioactive molecules. In nuclear medicine, HBED-based radiopharmaceuticals are used as powerful radiotracers for tumor imaging. Among variants of bifunctional HBED chelators, HBED-CC is the most well-known; it possesses two terminal carboxylic acid groups that are able to undergo bioconjugation by amide-bond formation. However, to permit bioconjugation through click coupling, we previously modified the structure of HBED-CC and introduced HBED-NN chelator bearing two azide functions. We have now combined the conjugation capabilities of HBED-CC and HBED-NN chelators in one molecule and have created HBED-NC, which possesses both azide and carboxylic acid groups. The advantage of HBED-NC is that it provides options for constructing either monomeric or heterodimeric radiolabeling precursors. This work describes the synthesis of HBED-NC by either of two pathways.


2017 ◽  
Vol 359 (17) ◽  
pp. 3014-3021 ◽  
Author(s):  
Babasaheb Sopan Gore ◽  
Gopal Chandru Senadi ◽  
Amol Milind Garkhedkar ◽  
Jeh-Jeng Wang

2016 ◽  
Vol 18 (3) ◽  
pp. 672-675 ◽  
Author(s):  
Abbas Maleki ◽  
Davood Nematollahi ◽  
Fereshteh Rasouli ◽  
Azam Zeinodini-Meimand

Electrochemical synthesis of novel 2-hydroxyacetamides was performed in a one-pot protocol including the oxygen activation, extradiol cleavage, lactonization and amide bond formation sequence without any catalyst and enzyme.


2011 ◽  
Vol 41 (9) ◽  
pp. 1257-1266 ◽  
Author(s):  
Cheng-Rong Lu ◽  
Bei Zhao ◽  
Ying-Peng Jiang ◽  
Hao Ding ◽  
Sheng Yang

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