105424-75-7Relevant articles and documents
Synthesis of orthogonally protected 1,2-diaminopropanoic acids by ring-opening of 3-unsubstituted N-activated aziridine 2-carboxylates with para-methoxybenzylamine: A study of the regioselectivity of the reaction
O'Brien, Keith,Kelleher, Fintan
, p. 6627 - 6630 (2013)
Orthogonally protected 1,2-diaminopropanoic acids (DAPs) have been synthesised in good yields by the ring-opening of 3-unsubstituted N-activated aziridine 2-carboxylates with para-methoxybenzylamine. The choice of both the N-activating group and ester alk
Functionalized pyrroles from vinylaziridines and alkynes via rhodium-catalyzed domino ring-opening cyclization followed by C[dbnd]C bond migration
Wan, Shu-Hao,Liu, Shiuh-Tzung
, p. 1166 - 1170 (2019)
Rhodium(I)-catalyzed intermolecular cycloadditions of alkynes with vinyl aziridines bearing a conjugated carbonyl group in the olefin moiety followed by the double migration resulted in the formation of pyrrole derivatives in a one pot fashion.
New methodology for the preparation of N-tosyl aziridine-2-carboxylates
Marzorati, Liliana,Barazzone, Giovana C.,Bueno Filho, Marco A.,Wladislaw, Blanka,Di Vitta, Claudio
, p. 6509 - 6513 (2007)
N-Tosyl aziridine-2-carboxylate methyl esters were prepared from methyl N-tosyl-l-serinate or N-tosyl-l-threoninate, tosyl chloride, and K2CO3, under phase-transfer catalysis (PTC) conditions. The same methodology, as applied to the
A practical, fast, and high-yielding aziridination procedure using simple Cu(II) complexes containing N-donor pyridine-based ligands
Mohr, Fabian,Binfield, Seth A.,Fettinger, James C.,Vedernikov, Andrei N.
, p. 4833 - 4839 (2005)
Four-coordinate dichlorocopper(II) complexes derived from di(2-pyridyl)methanes or pyridine itself exhibit high catalytic activity in aziridination of regular olefins with PhINTs in weakly coordinating chloroform in the presence of 1-2 equiv of NaBAr
Efficient Synthesis of N-Sulfonyl β -Arylmethylalaninates from Serine via Ring Opening of N-Sulfonyl Aziridine-2-carboxylate
Chaudhari, Prashant,Bari, Sanjay
, p. 401 - 412 (2015)
We report the efficient synthesis of N-sulfonyl β-arylalanines methyl ester through regioselective ring opening of N-protected aziridines by variety of heteroaryl C-nucleophiles. We have optimized synthesis of N-protected aziridines with versatile protecting groups to afford 4a-c, 6a, and 6b with moderate to good yields using sulfuryl chloride, triethyl amine, and toluene at -50 °C. The present work reports on the studies related to electronic effect of nitrogen substituent on aziridination from the inexpensive starting material DL-serine. The present investigation also reports the efficient synthesis of N-sulfonyl β-arylmethylalaninates (7a-e and 8a-e) by regioselective nucleophilic ring opening of N-sulfonamido-protected aziridines using various aryl moieties such as C-nucleophiles and Lewis acids (InCl3, FeCl3, Cu(OTf)2) as catalysts and some trials by ring opening using Grignard reagent. GRAPHICAL ABSTRACT.
Aziridine-2-carboxylic acid derivatives and its open-ring isomers as a novel PDIA1 inhibitors
Leite, Irena,Andrianov, Victor,Zelencova-Gopejenko, Diana,Loza, Einars,Kazhoka-Lapsa, Iveta,Domracheva, Ilona,Stoyak, Marta,Chlopicki, Stefan,Kalvins, Ivars
, p. 1086 - 1106 (2022/01/12)
[Figure not available: see fulltext.] Acyl derivatives of aziridine-2-carboxylic acid have been synthesized and tested as PDIA1 inhibitors. Calculations of charge value and distribution in aziridine ring system and some alkylating agents were performed. For the first time was found that acyl derivatives of aziridine-2-carboxylic acid are weak to moderately active PDIA1 inhibitors.
Asymmetric Synthesis of β2-Aryl Amino Acids through Pd-Catalyzed Enantiospecific and Regioselective Ring-Opening Suzuki–Miyaura Arylation of Aziridine-2-carboxylates
Takeda, Youhei,Matsuno, Tetsuya,Sharma, Akhilesh K.,Sameera,Minakata, Satoshi
supporting information, p. 10226 - 10231 (2019/07/18)
A Pd-catalyzed enantiospecific and regioselective ring-opening Suzuki–Miyaura arylation of aziridine-2-carboxylates was developed. The cross-coupling allows for the asymmetric preparation of enantioenriched β2-aryl amino acids, starting from co
