- Preparation of tetrazole-fused π-conjugated molecules and their fluorescence behavior
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New tetrazole-fused π-conjugated molecules were prepared from dibromobenzonitriles by repeated regioselective Sonogashira-Hagihara cross-coupling with acetylenes and intramolecular nucleophilic cyclizations. The conjugated tetracyclic compounds exhibited fluorescence with lifetimes of nanosecond order. From TD-DFT calculations, excited state wavefunctions of compounds indicated that the HOMO-1→LUMO and HOMO→LUMO+1 mainly became the first excited state (S0→S1) to contribute significantly to light emission.
- Hata, Takeshi,Hayashi, Yoshiki,Hasegawa, Yuki,Iwai, Masaaki,Ishii,, Ayumi,Hasegawa, Miki,Shigeta, Masayuki,Urabe, Hirokazu
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- Online Spectroscopic Investigations (FTIR/Raman) of Industrial Reactions: Synthesis of Tributyltin Azide and Hydrogenation of Chloronitrobenzene
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The utilization of online spectroscopic methods (FTIR/Raman) for the development and the monitoring of chemical processes was demonstrated with two important chemical reaction types. The synthesis of tri-n-butyltin azide takes place at the solid-liquid interface and is therefore very sensitive to changes of reaction conditions or surface properties. Traditional offline analysis should be avoided due to the high toxicity of the compounds. The concentration variations of all involved compounds were determined. In the same way, the synthesis of 2-chloroaniline was studied to detect the formation of an unstable intermediate (the hydroxylamine) which can lead to uncontrolled decomposition reactions. Online spectroscopy is an opportunity to obtain the information about a reaction system faster and more efficiently than with conventional methods. This allows the rapid optimization of safe chemical processes and provides information for process control.
- Wiss, Jacques,Zilian, Arne
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- A novel and efficient tributyltin azide-mediated synthesis of 1H-tetrazolylstilbenes from cyanostilbenes
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A novel and efficient route was established for the synthesis of a series of (Z)-5-(2-(heteroaryl-2-yl) and (Z)-5-(3-(heteroaryl-3-yl)-1-(phenyl)vinyl)-1H-tetrazoles (3a-g and 6a-f, respectively) from cyanostilbene analogs containing benzo[b]thiophene, be
- Penthala, Narsimha Reddy,Bommagani, Shobanbabu,Yadlapalli, Jaishankar,Crooks, Peter A.
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- Tin-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles: Homogeneous and Heterogeneous Procedures
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The preparation of 5-substituted 1H-tetrazoles was efficiently achieved by reaction of trimethylsilylazide with nitriles using a triorganotin alkoxide precatalyst. The reaction mechanism was first investigated using a homogeneous tributyltin derivative and was explored through experimental investigations and DFT calculations. A heterogeneous version was then developed using a polymer-supported organotin alkoxide and afforded an efficient method for the preparation of tetrazoles in high yields with an easy work-up and a residual tin concentration in the desired products compatible for pharmaceutical applications (less than 10 ppm). (Figure presented.).
- Chrétien, Jean-Mathieu,Kerric, Gaelle,Zammattio, Fran?oise,Galland, Nicolas,Paris, Michael,Quintard, Jean-Paul,Le Grognec, Erwan
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p. 747 - 757
(2019/01/04)
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- A reliable one-pot synthesis of aryl azides from aryl amines using organotin azides as effective and recoverable reagents
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A mild and mass-efficient procedure based on the one-pot diazotization-azidodediazoniation of aromatic amines is described. A wide range of aryl azides are obtained in moderate to high yields by using tributyltin azide as an effective and reusable azide source in the presence of p-toluenesulfonic acid at room temperature. The method was also successfully applied employing an insoluble polymer-supported organotin azide.
- Godoy Prieto, Leonela,Lo Fiego, Marcos J.,Chopa, Alicia B.,Lockhart, María T.
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supporting information
p. 26 - 32
(2016/12/18)
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- Synthesis of deuterium-labeled olmesartan and candesartan
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This paper describes the synthesis of deuterium-labeled olmesartan and candesartan. The two desired compounds both used [2H4] 2-cyano-4'-methyl-biphenyl as deuterium-labeled reagent, which was synthesized beforehand in two steps. [2H4] olmesartan was synthesized in six steps further with 17% overall yield, and [2H4] candesartan was synthesized in seven steps further with 13% overall yield. Copyright 2012 John Wiley & Sons, Ltd. This paper describes the synthesis of deuterium-labeled olmesartan and candesartan. The two desired compounds both used [2H4] 2-cyano-4'-methyl-biphenyl as deuterium-labeled reagent, which was synthesized beforehand in two steps. [ 2H4] olmesartan was synthesized in a further six steps with a 17% overall yield, and [2H4] candesartan was synthesized in a further seven steps with a 13% overall yield. Copyright
- Zhang, Chi,Shen, Zucheng,Tian, Lei,Chen, Liqin
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p. 401 - 405
(2013/01/15)
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- PROCESS FOR PURE IRBESARTAN
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The present invention provides an improved and commercially viable process for preparation of irbesartan intermediate, 1-[(2''-cyanobiphenyl-4-yl)methyl]-2-n-butyl-4-spirocyclopentane-2-imidazolin-5-one, substantially free of 1-[(2''-cyanobiphenyl-4-yl)methyl]-2-n-propyl-4-spirocyclopentane-2-imidazolin-5-one impurity, thereby producing irbesartan substantially free of the undesired propyl analog impurity, namely 2-propyl-3-[[2''-(1H-tetrazol-5-yl)[1,1''-biphenyl]-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one. The present invention also provides a process for preparation of irbesartan substantially free of tin content. The present invention further provides a commercially viable process for preparation of irbesartan in high purity and in high yield.
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(2009/07/17)
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- CRYSTALLINE 1-(CYCLOHEXYLOXYCARBONYLOXY) ETHYL 1-((2'-CYANOBIPHENYL-4-YL)METHYL)-2-ETHOXY-1H-BENZO[D]IMIDAZOLE-7-CARBOXYLATE AND A PROCESS FOR ITS PREPARATION
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The present invention relates to 1-(cyclohexyloxycarbonyloxy)ethyl 1-((2'-cyanobiphenyl-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate in crystalline form and a process for its preparation, which is useful intermediate in the preparation of candesartan cilexetil. The present invention also relates to the preparation of candesartan cilexetil and pharmaceutical composition comprising candesartan cilexetil.
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(2008/12/08)
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- ONE POT PROCESS FOR THE PREPARATION OF CANDESARTAN
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Present invention is to provide one pot synthesis of candesartan without isolating the ester intermediate.
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(2008/06/13)
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- IMPROVED PROCESS FOR PREPARING PURE VALSARTAN
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An improved process for the preparation of substantially pure valsartan employing suitable reagents such as chelating agent and reaction conditions.
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(2009/03/07)
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- AZOLE DERIVATIVES WITH ANTIMUSCARINIC ACTIVITY
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The present invention relates to compounds of formula (I) wherein R1, R2, x, X, Y and B are as defined in the description for the treatment of muscarinic acetylcholine receptor mediated diseases, in particular M3 muscarinic receptor mediated diseases.
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(2008/06/13)
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- Process for preparing valsartan
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A process for preparing valsartan.
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Page/Page column 5
(2008/06/13)
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- Angiotensin II antagonists
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This invention provides novel heterocyclic derivatives, their pharmaceutical formulations, and their use for antagonizing angiotensin II receptors in mammals.
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- Angiotensin II antagonist intermediates
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This invention provides novel heterocyclic derivatives, their pharmaceutical formulations, and their use for antagonizing angiotensin II receptors in mammals.
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- Benzo-fused lactams promote release of growth hormone
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There are disclosed certain novel compounds identified as benzo-fused lactams STR1 which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to increase the stature of those afflicted with a lack of a normal secretion of natural growth hormone. The compounds are prepared by substitution of an amino-lactam with a substituted amide function. Growth promoting compositions containing such benzo-fused lactams as the active ingredient thereof are also disclosed.
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