1600-49-3Relevant academic research and scientific papers
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.
About 1-triphenylmethyl-3-tert-butylaziridinone and some of its reactions [1]
Lengyel,Cesare,Karram,Taldone
, p. 997 - 1002 (2001)
A high-yield synthesis of 1-triphenylmethyl-3-tert-butylaziridinone (4), its physical and spectral proper- ties, the limits of its thermal stability, and reactions with methanol, benzylamine and sodium methoxide in methanol are described.
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
, 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.
Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions
Cioc, Rǎzvan C.,Preschel, Hans D.,Van Der Heijden, Gydo,Ruijter, Eelco,Orru, Romano V. A.
, p. 7837 - 7842 (2016/06/09)
Herein, we describe the versatile application of triphenylmethyl (trityl) isocyanide in multicomponent chemistry. This reagent can be employed as a cyanide source in the Strecker reaction and as convertible isocyanide in the preparation of N-acyl amino acids by Ugi 4CR/detritylation and free imidazo[1,2-a]pyridin-3-amines by a Groebke-Blackburn-Bienaymé 3CR condensation/deprotection protocol. The mechanisms of these three classical MCRs intersect at the common N-trityl nitrilium ion intermediate, whose predictable reactivity can be exploited towards chemoselective transformations. Fate of the nitrilium ion: The application of trityl isocyanide as a mechanistic tool to dissect different reaction pathways in multicomponent chemistry is described. This reagent can be employed as a cyanide source in the Strecker reaction and as a convertible isocyanide in the preparation of N-acyl amino acids by Ugi 4CR/detritylation and free imidazo[1,2-a]pyridin-3-amines by Groebke-Blackburn-Bienaymé 3CR condensation/deprotection. Chemoselective transformations were achieved by the rational choice of reaction conditions.
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.
About four new trityl-substituted α-lactams
Lengyel, Istvan,Cesare, Victor,Adam, Ian,Taldone, Tony
, p. 73 - 95 (2007/10/03)
This investigation comprises the synthesis, a description of the physical and spectroscopic properties, determination of the limits of thermal stability, and reactions with protic and aprotic nucleophiles of four new trityl-substituted α-lactams. With the exception of 3,3-dimethyl-1-tritylaziridin-2-one (4a), which is unstable at room temperature, all new compounds have been fully characterized.
Titanium(IV) Chloride Catalyzed Cyanation of Benzylic Halides With Trimethylsilyl Cyanide
Zieger, Herman E.,Wo, Shiming
, p. 3838 - 3840 (2007/10/02)
Six sterically hindered benzylic chlorides have been substituted with cyano groups in excellent yields with trimethylsilyl cyanide and titanium tetrachloride in methylene chloride.Both monochloro substrates such as diphenylmethyl chloride and triphenylmethyl chloride and dichloro substrates such as dichlorodiphenylmethane and sym-tetraphenylethylene dichloride were studied.Because isonitriles are plausible reaction intermediates, the isomerization of trityl isonitrile by TiCl4 and by trityl tetrafluoroborate was studied at 0 and -78 deg C.Both reagents catalyze conversion to triphenylacetonitrile at 0 deg C while only trityl tetrafluoroborate is effective at -78 deg C.It was also found that trityl tetrafluoroborate reacts with trimethylsilyl cyanide in the absence of TiCl4 to give triphenylacetonitrile in 96percent yield.
