- A facile synthesis of the intermediates of the bicyclic organic bases: DBU and TBD
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Intermediates of DBU and TBD, N-(3-aminoproply) - ε -caprolactam and bis- (3-aminopropyl)-amine were prepared by the hydrogenolysis of N-(2-cyanoethyl) - ε - caprolactam and di- (β-cyanoethyl)-amine respectively over Raney-Ni in the presence of NaBH4 under atmospheric pressure with mild condition and good yield.
- Cheng,Liu
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- PHENYLAMINOPYRIMIDINE AMIDE AUTOPHAGY INHIBITORS AND METHODS OF USE THEREOF
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Described herein are compounds that are inhibitors of autophagy and their use in the treatment of disorders such as cancers.
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Paragraph 0261-0262
(2020/11/23)
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- HETEROARYLAMINOPYRIMIDINE AMIDE AUTOPHAGY INHIBITORS AND METHODS OF USE THEREOF
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Described herein are compounds that are inhibitors of autophagy and their use in the treatment of disorders such as cancers. (I)
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Paragraph 000233
(2020/11/30)
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- Investigating the Underappreciated Hydrolytic Instability of 1,8-Diazabicyclo[5.4.0]undec-7-ene and Related Unsaturated Nitrogenous Bases
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The widespread use of amidine and guanidine bases in synthetic chemistry merits a thorough understanding of their chemical properties. The propensity of these reagents to hydrolyze under mild conditions and generate aminolactams and aminoureas, respectively, has not been adequately described previously. During the synthesis of uprifosbuvir (MK-3682), we became aware of this liability for 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) by observing the formation of an unexpected reaction impurity and traced the root cause to low levels of N-(3-aminopropyl)-?-caprolactam present in the commercial bottle. A controlled stability study over a period of two months at 25 °C demonstrated that, above a threshold water content, DBU steadily hydrolyzed over time. Rates of hydrolysis for DBU, 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), and N,N,N′,N′-tetramethylguanidine (TMG) in organic, aqueous, and mixed solvent systems were then measured to gain a more general appreciation of what conditions to avoid in order to maintain their integrity. Our findings indicate that these bases are hydrolytically unstable in unbuffered and very basic solutions but become significantly more stable in buffered solutions at pH values below 11.6.
- Hyde, Alan M.,Calabria, Ralph,Arvary, Rebecca,Wang, Xiao,Klapars, Artis
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supporting information
p. 1860 - 1871
(2019/10/11)
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- N-Heterocyclic Olefin Catalysis for the Ring Opening of Cyclic Amidine Compounds: A Pathway to the Synthesis of ?-Caprolactam- and γ-Lactam-Derived Amines
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For the first time, 1,2-dimethyl-3-ethylimidazolium iodide (1a) catalyzes the ring opening of the bicyclic amidine system of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or DBN (1,5-diazabicyclo[4.3.0]non-5-ene) on reaction with aldehydes. The mechanism here
- Peixoto, Daniela,Malta, Gabriela,Cruz, Hugo,Barroso, Sónia,Carvalho, Ana Luísa,Ferreira, Luísa M.,Branco, Paula S.
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p. 3793 - 3800
(2019/03/07)
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- Unexpected reactivity of graphene oxide with DBU and DMF
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An unusual reaction between GO, DBU and DMF, that typically uses base and solvent, has been thoroughly analyzed providing valuable basic knowledge about the reactivity of GO, which is essential to control functionalization and therefore the properties of
- Ramírez-Jiménez, Rafael,Franco, Mario,Rodrigo, Eduardo,Sainz, Raquel,Ferritto, Rafael,Lamsabhi, Al Mokhtar,Ace?a, José Luis,Cid, M. Belén
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supporting information
p. 12637 - 12646
(2018/07/13)
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- Synthesis of potentially bioactive PABA-related N-(aminoalkyl)lactamic amino acids and esters via selective SNAr reactions
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Potentially bioactive N-(aminoalkyl)lactamic amino acids and esters were synthesized in satisfactory to good yields by SNAr reactions of aromatic acids with N-(3-aminopropyl)lactams followed by esterification with tertiary amino alcohols. The addition-elimination SNAr mechanism was confirmed by NMR and MS measurements. Graphical Abstract: [Figure not available: see fulltext.]
- Goncalves, Renato S.,Abdelnur, Patricia V.,Santos, Vanessa G.,Simas, Rosineide C.,Eberlin, Marcos N.,Magalhaes, Alvicler,Perez Gonzalez, Eduardo R.
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experimental part
p. 197 - 204
(2011/10/05)
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- Branched non-covalent complexes between carboxylic acids and two tris(amidines)
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Carboxylic acids and two tris(amidine) bases formed branched 3:1 complexes with high solubility in chlorinated and aromatic solvents, particularly when aromatic carboxylic acids with suitable solubilising substituents were used. Whereas N,N′-diethylamidine complexes 10 proved to be difficult to isolate, the respective imidazoline complexes 14 were easily purified by crystallisation. Association constants were determined for model bis(imidazoline) complexes to be about 103 dm3 mol-1 in the competitive solvent mixture CDCl3-CD3OD (97:3).
- Kraft, Arno
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p. 705 - 714
(2007/10/03)
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- Amidine als Zwischenprodukte bei Umamidierungsreaktionen
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By loss of water in the presence of p-toluenesulfonic acid/xylol N-aminoalkyl-lactames form bicyclic amidines.The corresponding N-alkylaminoalkyl-lactames react to bicyclic amidinium salts or to transamidated products, ring-enlarged by the N-alkylamino re
- Heidelberger, Christian,Guggisberg, Armin,Stephanou, Euripides,Hesse, Manfred
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p. 399 - 406
(2007/10/02)
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