1600-49-3Relevant articles and documents
About the First Stable α-Lactam with a Secondary Alkyl Substituent in Position Three: 3-Isopropyl-1-triphenylmethylaziridinone
Benitez, Michael,Wang, Yun Dan,Lengyel, Istvan,Fitzsimmons, Matthew,Cesare, Victor
, p. 2877 - 2882 (2018)
A three-step synthesis, characterization, pyrolysis, the thermal decomposition products, and three reactions of 3-isopropyl-1-triphenylmethylaziridinone are described. This is the first stable α-lactam with a secondary alkyl substituent in position three.
Coupling Interrupted Fischer and Multicomponent Joullié-Ugi to Chase Chemical Diversity: from Batch to Sustainable Flow Synthesis of Peptidomimetics
Alfano, Antonella Ilenia,Buommino, Elisabetta,Ferraro, Maria Grazia,Irace, Carlo,Zampella, Angela,Lange, Heiko,Brindisi, Margherita
supporting information, p. 3795 - 3809 (2021/10/20)
The generation of peptidomimetic substructures for medicinal chemistry purposes requires effective and divergent synthetic methods. We present in this work an efficient flow process that allows quick modulation of reagents for Joullié-Ugi multicomponent reaction, using spiroindolenines as core motifs. This sterically hindered imine equivalent could successfully be diversified using various isocyanides and amino acids in generally good space-time yields. A telescoped flow process combining interrupted Fischer reaction for spiroindolenine synthesis and subsequent Joullié-Ugi-type modification resulted in product formation in very good overall yield in less than 2 hours compared to 48 hours required in batch mode. The developed protocol can be seen as a general tool for rapid and facile generation of peptidomimetic compounds. We also showcase preliminary biological assessments for the prepared compounds.
New one-step synthesis of isonitriles
Bardsley, Kathryn,Hagigeorgiou, Michael,Lengyel, Istvan,Cesare, Victor
supporting information, p. 1727 - 1733 (2013/05/09)
A new one-step synthesis of isonitriles is described. The starting materials are a primary amine, chloroform, sodium hydride, and the phase-transfer catalyst 15-crown-5 ether, and the solvent is benzene. Five compounds are used to illustrate the features of the new synthesis: 1-adamantyl isocyanide (2a), 2-adamantyl isocyanide (2b), cis-1,8- diisocyano-p-menthane (2c), 2,4,6-trimethylphenyl isocyanide (2d), and trityl isocyanide (2e). The present synthesis is superior to the existing published syntheses because of its yields are good, the by-products are innocuous (H2 gas and NaCl), and its workup is simple. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
