- A short synthesis of pyridines from deprotonated α-aminonitriles by an alkylation/RCM sequence
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α-Aminonitriles can serve as versatile key precursors for the synthesis of nitrogen containing heterocycles. After unsuccessful trials involving the [1,2]-Stevens rearrangement of nitrile-stabilized ammonium ylides, we herein report a simple three-step synthesis of substituted pyridines based on an alkylation/ring-closing metathesis/aromatization sequence.
- Weber, Carina,Nebe, Marco M.,Kaluza, Lukas P. V.,Opatz, Till
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p. 633 - 641
(2016/07/06)
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- Palladium-catalyzed γ-selective arylation of zincated Boc-allylamines
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The regio- and diastereoselective arylation of Boc-protected allylamines was performed via a one-pot lithiation/transmetalation to zinc/cross-coupling sequence, through an appropriate choice of a phosphine ligand. A variety of γ-arylated products were obtained in moderate to good yield, and the products could be directly transformed into valuable γ-arylamines and β-aryl aldehydes.
- Millet, Anthony,Baudoin, Olivier
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supporting information
p. 3998 - 4000
(2014/08/18)
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- 3-HYDROXYPYRROLIDINE INHIBITORS OF 5?-METHYLTHIOADENOSINE PHOSPHORYLASE AND NUCLEOSIDASE
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The present invention relates to 3-hydroxypyrrolidine compounds of the general formula (I) which are inhibitors of 5?-methylthioadenosine phosphorylase or 5?-methylthioadenosine nucleosidase. The invention also relates to the use of these compounds in the treatment of diseases or conditions in which it is desirable to inhibit 5?-methylthioadenosine phosphorylase or 5?-methylthioadenosine nucleosidase including cancer, and to pharmaceutical compositions containing the compounds
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Page/Page column 41-42
(2011/02/24)
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- COMPOUNDS AND COMPOSITIONS FOR TREATMENT OF CANCER
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Compounds and compositions for treating, preventing or managing cancer are disclosed. The compositions provided herein comprise SNS-595 and N-desmethyl-SNS-595. Also provided are pharmaceutical compositions comprising the compounds and methods of treatment using the compounds and compositions.
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Page/Page column 16
(2010/03/02)
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- Molecular iodine-catalyzed facile procedure for N-Boc protection of amines
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An efficient and practical protocol for the protection of various structurally and electronically divergent aryl and aliphatic amines using (Boc)2O in the presence of a catalytic amount of molecular iodine (10 mol%) under solvent-free conditions at ambient temperature is presented.
- Varala, Ravi,Nuvula, Sreelatha,Adapa, Srinivas R.
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p. 8283 - 8286
(2007/10/03)
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- Technical scale synthesis of a new and highly potent thrombin inhibitor
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In this account, we describe the development of an efficient and convergent process for the peptidomimetic thrombin inhibitor 1 on production plant scale. Starting from nicotinonitrile (13), (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2- pyrrolidinecarboxylic acid (5) and (2R)-2-amino-3-cyclohexylpropanoic acid (29) compound 1 was obtained in 16 chemical steps. New methods had been developed for the preparation of the key intermediate dehydroproline 22 and the transformation of nitriles into amidines. The thrombin inhibitor 1 was isolated by special techniques (nanofiltration and spray drying). Almost all salts of 1 are amorphous, however, a crystalline complex was obtained with 1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Saccharin).
- Bernard, Harald,Buelow, Gerd,Lange, Udo E. W.,Mack, Helmut,Pfeiffer, Thomas,Schaefer, Bernd,Seitz, Werner,Zierke, Thomas
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p. 2367 - 2375
(2007/10/03)
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- A short and efficient synthesis of (S)-1-Boc-2,5-dihydro-1H-pyrrole-2-carboxylic acid
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A short and efficient synthesis of (S)-1-Boc-2,5-dihydro-1H-pyrrole-2-carboxylic acid is described. Starting from N-Boc-diallylamine, the synthesis involves ring-closing metathesis (RCM), directed alkoxycarbonylation (using strong lithium bases and alkyl carbonates) and enzymatic kinetic resolution of the racemate.
- Stuermer,Schaefer,Wolfart,Stahr,Kazmaier,Helmchen
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