- Facile Access to 1,4-Disubstituted Pyrrolo[1,2- a ]pyrazines from α-Aminoacetonitriles
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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.
- 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
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supporting information
p. 441 - 449
(2020/01/23)
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- Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions
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Gold-catalyzed oxidative couplings of two indoles and one α-cyano gold carbene to form bis(indolyl)methane derivatives are described. Two different indoles are compatible with these reactions to provide reasonable yields. A plausible mechanism is postulated to rationalize the experimental data including product distributions, D2O labeling, and the significant effects of gold catalysts and cyano groups.
- Singh, Rahulkumar Rajmani,Liu, Rai-Shung
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supporting information
p. 4593 - 4596
(2017/04/28)
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- Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides to yield 1-amino-1H-indenes
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Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides yield 1-amino-1H-indenes in two distinct pathways; the success of these annulations relies on the high electrophilicity of α-cyano arylgold carbenes to activate an ionic pathway.
- Singh, Rahulkumar Rajmani,Pawar, Samir Kundlik,Huang, Min-Jie,Liu, Rai-Shung
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supporting information
p. 11434 - 11437
(2016/09/23)
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- PYRROLO [2,3-D] PYRIMIDIN DERIVATIVES AS PROTEIN KINASE B INHIBITORS
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The invention relates to a novel group of compounds of Formula (I) or salts thereof: wherein Y, Z1, Z2, R1, R4, R5 and n are as described in the specification, which may be useful in the treatment or prevention of a disease or medical condition mediated through protein kinase B (PKB) such as cancer. The invention also relates to pharmaceutical compositions comprising said compounds, methods of treatment of diseases mediated by PKB using said compounds and methods for preparing compounds of Formula (I)
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Page/Page column 85-86
(2009/05/30)
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- AMIDES AND METHOD FOR PLANT DISEASE CONTROL WITH THE SAME
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N-(α-cyanobenzyl)amide compounds represented by the formula (1): wherein R1 represents a hydrogen atom; a halogen atom; a C1-C6 alkyl group optionally substituted with a halogen atom or the like; or the like, R2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group or the like, R3 represents a hydrogen atom or the like, R4 represents a C1-C4 alkyl group, a C3-C4 alkenyl group or the like, R5 represents a C1-C4 alkyl group, a C3-C4 alkenyl group, or the like, R6 represents a hydrogen atom or the like, R7 represents a hydrogen atom or the like, R8 represents a hydrogen atom or the like, R9 represents a hydrogen atom or the like, R10 represents a hydrogen atom or the like, R11 represents a hydrogen atom or the like, and R12 represents a hydrogen atom or the like, have excellent control activities against plant diseases.
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Page/Page column 76
(2010/11/08)
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- Fungicidal Composition
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A fungicidal composition comprising: an amide compound represented by formula (1) and dimethomorph as active ingredients, and a method for controlling plant diseases applying effective amount of an amide compound represented by formula (1) and dimethomorph to plant(s) or soil where plant(s) are growing.
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Page/Page column 15-16
(2010/02/15)
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- Development of a new α-aminonitrile synthesis
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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.
- Chu, Guo-Hua,Gu, Minghua,Gerard, Baudouin,Dolle, Roland E.
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p. 4583 - 4590
(2007/10/03)
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- Highly efficient and enantioselective synthesis of L-arylglycines and D-arylglycine amides from biotransformations of nitriles
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Under very mild conditions, the Rhodococcus sp. AJ270-catalysed biotransformation of arylglycine nitriles 1, prepared easily from the reaction of substituted benzaldehydes, ammonium chloride and potassium cyanide, proceeded efficiently to produce optically active D-arylglycine amides 2 and L-arylglycines 3 in excellent yields with enantiomeric excesses higher than 99%.
- Wang, Mei-Xiang,Lin, Shuang-Jun
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p. 6925 - 6927
(2007/10/03)
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- Phenyl Tetraacetic Acid Ligands for Gadolinium: Potential Magnetic Resonance Image Enhancing Agents
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Three new ligands suitable for chelation to gadolinium have been synthesized.N,N'->bis and N,N'->bis were prepa
- McLaren, Ashley B.,Baker, Richmond J.,Wilson, J. Gerald
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p. 449 - 454
(2007/10/02)
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