The chemistry of thujone. XVI. Versatile and efficient routes to safronitrile, β-cyclogeranonitrile, β-cyclocitral, damascones, and their analogues

1992 ◽  
Vol 70 (7) ◽  
pp. 2094-2114 ◽  
Author(s):  
James P. Kutney ◽  
Philip J. Gunning ◽  
Robin G. Clewley ◽  
John Somerville ◽  
Steven J. Rettig
Keyword(s):  
Starting Material ◽  
Forest Industry ◽  
Synthetic Route ◽  
Rose Oil ◽  
Efficient Route ◽  
Synthetic Sequence

Thujone, a waste by-product of the Canadian forest industry, has been utilized as a starting material to develop a versatile synthetic route to the damascones (rose oil ketones) and related analogues. The synthetic sequence provides a route to β-cyclocitral (45), the latter having been previously converted to β-damascone (2). In addition, thujone-derived intermediates are converted to β-damascenone (48) and to intermediates that can be utilized for the preparation of damascone analogues. In conjunction with the above, an efficient route to safronitrile (42), β-cyclogeranonitrile (43), and β-cyclocitral (45) from 2,6-dimethylcyclohexanone has been developed. In summary, these studies afford an attractive versatile route to these important perfumery materials.

A Meso-Substituted Tripyrrin Metal Complex as the Candidate for Fluorescent Material

2012 ◽  
Vol 557-559 ◽  
pp. 665-668 ◽  
Author(s):  
Peng Peng Liu ◽  
Ya Qing Feng ◽  
Cheng Zhi Gu ◽  
Cheng Jie Li ◽  
Shu Xian Meng ◽  
...  
Keyword(s):  
Metal Complex ◽  
Fluorescent Property ◽  
Starting Material ◽  
Synthetic Chemistry ◽  
Synthetic Route ◽  
Compound A ◽  
Fluorescent Material ◽  
Fluorescent Materials ◽  
Strong Candidate

We herein report the synthesis of bis-(5,10-diphenyltripyrrin)nickel(II), which is the first meso-substituted tripyrrin metal complex. The use of tripyrrane as the starting material provides a new synthetic route to tripyrrins. The functionalization on the meso positions endows this type of compound a brighter perspective in synthetic chemistry. Meanwhile, the fluorescent property of the compound has been detected, indicating that this type of compound a strong candidate for fluorescent materials.

scholarly journals Diastereoselective Synthesis of (–)-Bestatin, Epibestatin, Phebestin and (3S,4R)-4-Amino-3-hydroxy-5-phenylpentanoic Acid from an Aldehyde Derived from d-Phenylalanine

SynOpen ◽  
2019 ◽  
Vol 03 (04) ◽  
pp. 114-123
Author(s):  
Vipin Kumar Jain
Keyword(s):  
Amino Acid ◽  
Efficient Method ◽  
Good Yield ◽  
Starting Material ◽  
Hydroxyl Group ◽  
Diastereoselective Synthesis ◽  
Synthetic Route ◽  
Protected Amino Acid ◽  
Very High ◽  
General Method

A convenient and efficient method for the synthesis of (–)-bestatin, epibestatin, phebestin, and (3S,4R)-4-amino-3-hydroxy-5-phenylpentanoic acid is reported. The key step is a proline-catalyzed α-hydroxylation of an aldehyde derived from d-phenylalanine, which leads to incorporation of a hydroxyl group at the α-position of that aldehyde with good yield and very high diastereoselectivity. Bestatin and its dia­stereomer epibestatin are synthesized from the same starting material using the same sequence of reactions, except for proline as the catalyst. An O-MOM and Boc-protected amino acid, a common intermediate for bestatin, was coupled with a dipeptide, H-Val-Phe-OMe followed by global deprotection to yield phebestin. (3S,4R)-4-Amino-3-hydroxy-5-phenylpentanoic acid was also synthesized in eight steps from the same starting material. The reported synthetic route offers a general method for the synthesis of such types of compounds and their analogues by changing the proline catalyst and/or the starting material from d- to l-phenylalanine.

Preparation and Characterization of Novel Methyl Acrylate

2011 ◽  
Vol 343-344 ◽  
pp. 1236-1241
Author(s):  
Yong En Guo ◽  
Jing Cao ◽  
Cai Ju Zhou ◽  
Shao Peng Wen ◽  
Ya Mei Zhang ◽  
...  
Keyword(s):  
1H Nmr ◽  
Methyl Acrylate ◽  
Salvianolic Acid B ◽  
Starting Material ◽  
Synthetic Route ◽  
Target Compound ◽  
Pharmacological Activities ◽  
Salvianolic Acid ◽  
Important Intermediate

Salvianolic acid B has many important pharmacological activities. A novel synthetic route of methyl acrylate derivative—an important intermediate to synthesize salvianolic acid B, was designed, and the target compound was prepared in seven steps of reactions with 2-bromo-3-hydroxy-4-methoxybenzaldehyde as major starting material. Its and other four important unreported intermediates’ structures were characterized by IR, 1H NMR, MS, etc.

Efficient synthesis of 4-amino-2,6-dichloropyridine and its derivatives

2016 ◽  
Vol 22 (5) ◽  
Author(s):  
Congming Ma ◽  
Zuliang Liu ◽  
Qizheng Yao
Keyword(s):  
Starting Material ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Important Intermediate

AbstractA facile synthetic route to an important intermediate 4-amino-2,6-dichloropyridine was developed. Oxidation of 2,6-dichloropyridine as a starting material gave pyridine

The Efficient Synthesis of 2-(3-Carbamoylpyridine-2-yl) nicotinamide Pyridine Salts

2021 ◽  
Vol 18 ◽  
Author(s):  
Lei-Yang Zhang ◽  
Jing-Bo Geng ◽  
Nai-Xing Wang ◽  
Yue-Hua Wu ◽  
Zhan Yan ◽  
...  
Keyword(s):  
Starting Material ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Chiral Compound ◽  
Axial Chirality ◽  
Simple Operation ◽  
Chiral Compounds ◽  
Axially Chiral

: The synthesis of axially chiral compounds has attracted a great deal of attention in the recent years. Herein, an efficient and economical synthetic route has been developed for 2-(3-carbamoylpyridin-2-yl) nicotinamide pyridine salts, an axially chiral compound. The starting material 1,10-phenanthroline has been readily available and 2-(3-carbamoylpyridin-2-yl) nicotinamide pyridine salts have been obtained in moderate to good yields. This protocol features simple operation and easy scalability. In addition, the axial chirality of the products has also been preliminary studied.

A short synthetic route towards merosesquiterpenes with a benzoxanthene skeleton

2014 ◽  
Vol 50 (86) ◽  
pp. 13100-13102 ◽  
Author(s):  
Antonio Fernández ◽  
Esteban Alvarez ◽  
Ramón Alvarez-Manzaneda ◽  
Rachid Chahboun ◽  
Enrique Alvarez-Manzaneda
Keyword(s):  
Diels Alder ◽  
Synthetic Route ◽  
Target Compound ◽  
Synthetic Sequence

A short synthetic sequence for the preparation of merosesquiterpenes with a benzoxanthene skeleton starting from (−)-sclareol is reported. The D ring of the target compound is obtained through a Diels–Alder cycloaddition.

scholarly journals A Multidisciplinary Investigation to Determine the Structure and Source of Dimeric Impurities in AMG 517 Drug Substance

2009 ◽  
Vol 2009 ◽  
pp. 1-12 ◽  
Author(s):  
Maria Victoria Silva Elipe ◽  
Zhixin Jessica Tan ◽  
Michael Ronk ◽  
Tracy Bostick
Keyword(s):  
Hplc Analysis ◽  
Scale Up ◽  
2D Nmr ◽  
Starting Material ◽  
Drug Substance ◽  
Synthetic Route ◽  
Stress Studies ◽  
Experimental Drug ◽  
Initial Scale

In the initial scale-up batches of the experimental drug substance AMG 517, a pair of unexpected impurities was observed by HPLC. Analysis of data from initial LC-MS experiments indicated the presence of two dimer-like molecules. One impurity had an additional sulfur atom incorporated into its structure relative to the other impurity. Isolation of the impurities was performed, and further structural elucidation experiments were conducted with high-resolution LC-MS and 2D NMR. The dimeric structures were confirmed, with one of the impurities having an unexpected C-S-C linkage. Based on the synthetic route of AMG 517, it was unlikely that these impurities were generated during the last two steps of the process. Stress studies on the enriched impurities were carried out to further confirm the existence of the C-S-C linkage in the benzothiazole portion of AMG 517. Further investigation revealed that these two dimeric impurities originated from existing impurities in the AMG 517 starting material, N-acetyl benzothiazole. The characterization of these two dimeric impurities allowed for better quality control of new batches of the N-acetyl benzothiazole starting material. As a result, subsequent batches of AMG 517 contained no reportable levels of these two impurities

A New Approach for the Synthesis of 6,7-Dihydro-5H-Cyclopenta[b]pyridine

2013 ◽  
Vol 634-638 ◽  
pp. 1211-1214
Author(s):  
Jin Hua Zhou ◽  
Hai Li Gao ◽  
Han Zhou Sun ◽  
Yu Xiong Wu
Keyword(s):  
1H Nmr ◽  
Nucleophilic Addition ◽  
Raw Materials ◽  
Total Yield ◽  
Target Product ◽  
Synthetic Route ◽  
Reaction Conditions ◽  
Nmr Spectrum ◽  
New Approach ◽  
Efficient Route

A new practical and efficient route was developed for the synthesis of 6,7-dihydro-5H-cyclopenta[b]pyridine, which is a key intermediate of cefpirome. Leading to the formation of the corresponding product, nucleophilic addition, acetylization, Vilsmeier cyclization reaction and dechlorination were employed under mild reaction conditions by using commercially available cyclopentanone and benzylamine as raw materials. The total yield of this newly developed synthetic route for the target product was 43.15% with 99.7% of purity (HPLC). The structure of target molecular was confirmed by LC-MS and 1H NMR spectrum.

scholarly journals A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

2014 ◽  
Vol 10 ◽  
pp. 1390-1396 ◽  
Author(s):  
Martin Popr ◽  
Simona Hybelbauerová ◽  
Jindřich Jindřich
Keyword(s):  
Chromatographic Separation ◽  
Functional Group ◽  
Single Step ◽  
Starting Material ◽  
Scale Production ◽  
Synthetic Route ◽  
Complete Series ◽  
Work Up ◽  
Derivatives Of

An efficient synthetic route toward the preparation of a complete series of monosubstituted tetraalkylammonium cyclodextrin (CD) derivatives is presented. Monotosylation of native CDs (α-, β-, γ-) at position 6 gave the starting material. Reaction of monotosylate (mono-Ts-CD) with 45% aqueous trimethylamine gave CDs substituted with one cationic functional group in a single step. Derivatives equipped with a substituent containing two cationic sites separated by an ethylene or a propylene linker were prepared by reacting mono-Ts-CD with neat N,N,N’-trimethylethane-1,2-diamine or N,N,N’-trimethylpropane-1,3-diamine and subsequent methylation by CH3I in good yields. Finally, analogues bearing a moiety with three tetraalkylammonium sites were synthesized by reacting mono-Ts-CD with bis(3-aminopropyl)amine and subsequent methylation. The majority of the presented reactions are very straightforward with a simple work-up, which avoids the need of chromatographic separation. Thus, these reactions are suitable for the multigram-scale production of monosubstituted cationic CDs.

Hexaaryl-carbo-benzenes revisited: a novel synthetic route, crystallographic data, and prospects of electrochemical behavior

2017 ◽  
Vol 41 (10) ◽  
pp. 3908-3914 ◽  
Author(s):  
Chongwei Zhu ◽  
Carine Duhayon ◽  
Daniel Romero-Borja ◽  
José-Luis Maldonado ◽  
Gabriel Ramos-Ortíz ◽  
...  
Keyword(s):  
Thin Films ◽  
Charge Transport ◽  
Transport Properties ◽  
Electrochemical Behavior ◽  
Crystallographic Data ◽  
Synthetic Route ◽  
Efficient Route

Hexaphenyl-carbo-benzene and a substituted homologue were prepared via an efficient route, and characterized by crystallography and voltammetry with the view of studying charge transport properties within thin films.

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