42456-26-8Relevant academic research and scientific papers
Facile Access to 1,4-Disubstituted Pyrrolo[1,2- a ]pyrazines from α-Aminoacetonitriles
Basha, Mushkin,Belema, Makonen,Dhar, T. G. Murali,Gupta, Anuradha,Gupta, Arun Kumar,Indasi, Gopi Kumar,Karmakar, Ananta,Mathur, Arvind,Meanwell, Nicholas A.,Ramalingam, Sridharan,Rampulla, Richard
supporting information, p. 441 - 449 (2020/01/23)
An efficient and practical synthetic protocol for the synthesis of 1,4-disubstituted pyrrolo[1,2- a ]pyrazine derivatives is described that originates from α-substituted pyrroloacetonitriles which, in turn, are readily available from aryl and alkyl aldehydes. The α-pyrroloacetonitriles were subjected to a Friedel-Crafts acylation with methyl chlorooxoacetate followed by reduction of the nitrile group under Pd-catalyzed hydrogenation conditions and finally aromatization with DDQ leading to the desired pyrrolo[1,2- a ]pyrazine derivatives. This method was generalized and successfully applied to various aryl, heteroaryl, and alkyl substrates. The developed protocol provides direct and convenient access to 1,4-disubstituted ring systems in moderate to good overall yields (51-68percent) without the need for purification of the intermediates. Further functionalization via the stepwise halogenation (bromination, iodination) and nitration was also demonstrated. In addition, the potential of the ester functionality for elaboration was demonstrated by manipulating into heterocyclic ring systems, exemplified by conversion into benzoxazole derivatives.
Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia
Li, Qing-Hua,Li, Zhao-Feng,Tao, Jing,Li, Wan-Fang,Ren, Li-Qing,Li, Qian,Peng, Yun-Gui,Liu, Tang-Lin
supporting information, p. 8429 - 8433 (2019/10/14)
α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.
A Sustainable, Semi-Continuous Flow Synthesis of Hydantoins
Vukeli?, Stella,Koksch, Beate,Seeberger, Peter H.,Gilmore, Kerry
supporting information, p. 13451 - 13454 (2016/09/13)
Hydantoins are an important class of heterocycles with applications in pharmacy, agriculture, and as intermediates in organic synthesis. Traditional synthetic procedures to access hydantoins are target oriented with multiple synthetic steps and often use reagents that are not commercially available or sustainable. Herein, an efficient process is described for accessing hydantoins starting from commercially available amines using consecutive gas–liquid transformations (oxygen, carbon dioxide). This semi-continuous process produced ten benzylic/aliphatic hydantoins in good overall yields (52–84 %).
Efficient asymmetric synthesis of 1-cyano-tetrahydroisoquinolines from lipase dual activity and opposite enantioselectivities in α-aminonitrile resolution
Sakulsombat, Morakot,Vongvilai, Pornrapee,Ramstr?m, Olof
supporting information, p. 11322 - 11325 (2014/10/15)
Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic α-aminonitrile compounds are described. α-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, where opposite enantioselectivities could be recorded for certain substrates. Dynamic chemistry: Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic α-aminonitrile compounds are described. α-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, in which opposite enantioselectivities could be recorded for certain substrates (see scheme).
Development of a new α-aminonitrile synthesis
Chu, Guo-Hua,Gu, Minghua,Gerard, Baudouin,Dolle, Roland E.
, p. 4583 - 4590 (2007/10/03)
α-Aminonitriles are prepared upon reaction of aryl carboxaldehydes with LiHMDS and acetone cyanohydrin. This new method provides a general route to the synthesis of various substituted α-aminoarylacetonitriles in high yield and purity, and avoids the use of the highly toxic cyanide salts.
Process for producing 2-amino-2-arylacetonitriles
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, (2008/06/13)
The present invention is directed to a process for producing 2-amino-2-arylacetonitriles of general formula I: STR1 wherein R and R1 independently represent hydrogen, hydroxy, hydroxy(C1 -C4)alkyl, (C1 -C4)alkoxy, (C1 -C6)alkyl, 2-furyl, 2-thienyl, 4-pyridinyl, 1-pyrrolydinyl, 1-piperidinyl, 4-morpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl, 4-phenylpiperazinyl, or phenyl which can optionally be substituted with from 1 to 3 substituents independently selected from (C1 -C4)alkyl and (C1 -C4)alkoxy, or R and R1 independently represent a phenyl(C1 -C4)alkyl or a phenyl(C1 -C4)alkoxy group wherein the phenyl group can be either unsubstituted or substituted as above. An arylaldehyde derivative of formula II STR2 is reacted with chloroform in base and in the presence of ammonia to give the 2-amino-2-arylacetonitrile derivative.
