158223-55-3Relevant academic research and scientific papers
The two component palladium catalyst system for intermolecular hydroamination of allenes
Al-Masum, Mohammad,Meguro, Masaki,Yamamoto, Yoshinori
, p. 6071 - 6074 (1997)
The combination of acetic acid with Pd2(dba)3.CHCl3 and dppf [1.1'-Bis(diphenylphosphino ferrocene)] is a new type of catalytic system, capable of effecting the addition of protected and/or functionalized amines to allenes
Direct use of allylic alcohols and allylic amines in palladium-catalyzed allylic amination
Jing, Jiangyan,Huo, Xiaohong,Shen, Jiefeng,Fu, Jingke,Meng, Qinghua,Zhang, Wanbin
, p. 5151 - 5154 (2017/07/12)
Allylic alcohols and allylic amines were directly utilized in a Pd-catalyzed hydrogen-bond-activated allylic amination under mild reaction conditions in the absence of any additives. The cooperative action of a Pd-catalyst and a hydrogen-bonding solvent is most likely responsible for its high reactivity. The catalytic system is compatible with a variety of functional groups and can be used to prepare a wide range of linear allylic amines in good to excellent yields. Furthermore, this methodology can be easily applied to the one-step synthesis of two drugs, cinnarizine and naftifine, on a gram scale.
A metagenomics approach for new biocatalyst discovery: Application to transaminases and the synthesis of allylic amines
Baud, Damien,Jeffries, Jack W. E.,Moody, Thomas S.,Ward, John M.,Hailes, Helen C.
, p. 1134 - 1143 (2017/08/14)
Transaminase enzymes have significant potential for the sustainable synthesis of amines using mild aqueous reaction conditions. Here a metagenomics mining strategy has been used for new transaminase enzyme discovery. Starting from oral cavity microbiome samples, DNA sequencing and bioinformatics analyses were performed. Subsequent in silico mining of a library of contiguous reads built from the sequencing data identified 11 putative Class III transaminases which were cloned and overexpressed. Several screening protocols were used and three enzymes selected of interest due to activities towards substrates covering a wide structural diversity. Transamination of functionalized cinnamaldehydes was then investigated for the production of valuable amine building blocks.
Rhodium/Yanphos-Catalyzed Asymmetric Interrupted Intramolecular Hydroaminomethylation of trans-1,2-Disubstituted Alkenes
Chen, Caiyou,Jin, Shicheng,Zhang, Zhefan,Wei, Biao,Wang, Heng,Zhang, Kai,Lv, Hui,Dong, Xiu-Qin,Zhang, Xumu
supporting information, p. 9017 - 9020 (2016/08/05)
The first interrupted asymmetric hydroaminomethylation reaction was developed. The challenging trans-1,2-disubstituted olefins were employed as substrates, and a series of valuable chiral pyrrolidinones and pyrrolidines were obtained in high yields with high regioselectivities and excellent enantioselectivities. Several synthetic transformations were conducted, demonstrating the high synthetic utility of our method. A creative route for the synthesis of vernakalant and Enablex was also developed.
A catalytic asymmetric chlorocyclization of unsaturated amides
Jaganathan, Arvind,Garzan, Atefeh,Whitehead, Daniel C.,Staples, Richard J.,Borhan, Babak
, p. 2593 - 2596 (2011/05/02)
The asymmetric chlorocyclization of unsaturated amides catalyzed by (DHQD)2PHAL yields oxazoline and dihydrooxazine derivatives (see scheme). The reaction is operationally simple and employs 1-2 mol % of the commercially available (DHQD)2PHAL (hydroquinidine 1,4-phthalazinediyl diether) catalyst. Different substitution patterns of the olefin as well as aromatic and aliphatic olefin substituents are well tolerated. DCDPH=N,N-dichloro-5,5-diphenylhydantoin. Copyright
4-Substituted 5-nitroisoquinolin-1-ones from intramolecular Pd-catalysed reaction of N-(2-alkenyl)-2-halo-3-nitrobenzamides
Dhami, Archana,Mahon, Mary F.,Lloyd, Matthew D.,Threadgill, Michael D.
experimental part, p. 4751 - 4765 (2009/10/23)
4-Methyl- and 4-benzyl-5-aminoisoquinolin-1-ones are close analogues of the water-soluble PARP-1 inhibitor 5-AIQ. Their synthesis was approached through Pd-catalysed cyclisations of N-(2-alkenyl)-2-iodo-3-nitrobenzamides. Reaction of N,N-diallyl-2-iodo-3-nitrobenzamide with Pd(PPh3)4 gave a mixture of 2-allyl-4-methyl-5-nitroisoquinolin-1-one and 2-allyl-4-methylene-5-nitro-3,4-dihydroisoquinolin-1-one. N-Benzhydryl-N-cinnamyl-2-iodo-3-nitrobenzamide similarly gave 2-benzhydryl-4-benzyl-5-nitroisoquinolin-1-one and 2-benzhydryl-4-benzylidene-5-nitro-3,4-dihydroisoquinolin-1-one. The isomeric products are not interconvertible. A deuterium-labelling study indicated that the isomers were formed by different pathways: a π-allyl-Pd route and the classical Heck route. The corresponding secondary amides N-allyl-2-iodo-3-nitrobenzamide and N-((substituted)-cinnamyl)-2-iodo-3-nitrobenzamide gave good yields of the required 4-methyl- and 4-((substituted)-benzyl)-5-nitroisoquinolin-1-ones, respectively, under optimised conditions (Pd(PPh3)4, Et3N, Bu4NCl, 150 °C, rapid heating). Hydrogenation of the nitro groups gave 4-methyl- and 4-benzyl-5-aminoisoquinolin-1-ones, which were potent inhibitors of PARP-1 activity.
1-Aza-1,3-bis(triphenylphosphoranylidene)propane: A Novel =CHCH2N= Synthon
Katritzky, Alan R.,Jiang, Jinlong,Steel, Peter J.
, p. 4551 - 4555 (2007/10/02)
1-Aza-1,3-bis(triphenylphosphoranylidene)propane (3), prepared in situ by the reaction of 1-methyl>benzotriazole (betmip, 4) with methylidenetriphenylphosphorane followed by treatment with butyllithium, enables convenient preparations of 3H-2-benzazepine (7), 2,3-diarylpyrroles 8, and primary allylamines 12 and 13.
