Convenient new synthesis of 1,3-diaroylureas

1969 ◽  
Vol 47 (11) ◽  
pp. 2097-2099 ◽  
Author(s):  
James F. Wolfe ◽  
George B. Trimitsis
Keyword(s):  
Sodium Hydride ◽  
Aromatic Esters ◽  
New Synthesis ◽  
Excess Sodium

It has been found that symmetrical 1,3-diaroylureas can be prepared in good yields by allowing urea to react with aromatic esters and excess sodium hydride in refluxing 1,2-dimethoxyethane. Applications of this method to the synthesis of unsymmetrical 1,3-diaroylureas and substituted monoaroylureas are also described.

Synthesis of 3-amino- and 3-azidoanalogs of 9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine (HPMPA)

1989 ◽  
Vol 54 (2) ◽  
pp. 446-454 ◽  
Author(s):  
Antonín Holý
Keyword(s):  
Acid Hydrolysis ◽  
Sodium Salt ◽  
Catalytic Hydrogenation ◽  
Alkaline Hydrolysis ◽  
Benzoyl Chloride ◽  
Sodium Hydride ◽  
Acid Catalyzed ◽  
Excess Sodium ◽  
Chloride Treatment

1-Azidopropane-2,3-diol (IIb) reacts with p-toluenesulfonyl chloride to give the tosyl derivative IIIa which, on acid catalyzed condensation with 2,3-dihydropyran, afforded 1-azido-2-(tetrahydropyran-2-yloxy-3-(p-toluenesulfonyloxy)propane (IIIb). Treatment of adenine sodium salt with IIIb resulted in the intermediate IV which was transformed by acid hydrolysis to 9-(RS)-(3-azido-2-hydroxypropyl)adenine (V). Catalytic hydrogenation of V led to 9-(RS)-(3-amino-2-hydroxypropyl)adenine (VI). 9-(RS)-(3-Azido-2-hydroxypropyl)-N6-benzoyladenine (VII) was obtained from V by chlorotrimethylsilane/benzoyl chloride treatment. Reaction of the compound VII with dimethyl p-toluenesulfonyloxymethanephosphonate (VIII) in the presence of excess sodium hydride, followed by alkaline hydrolysis, afforded methyl 9-(3-azido-2-phosphonylmethoxypropyl)adenine (IXa) which was transformed to the parent acid IXb by bromotrimethylsilane treatment. Hydrogenolysis of IXb yielded 9-(RS)-(3-amino-2-phosphonylmethoxypropyl)adenine (X).

ChemInform Abstract: Sodium Hydride as a Nucleophilic Agent. Part 1. A New Synthesis of 2,3′ -Biquinolyls

ChemInform ◽  
2010 ◽  
Vol 23 (31) ◽  
pp. no-no
Author(s):  
A. V. AKSENOV ◽  
I. V. MAGEDOV ◽  
YU. I. SMUSHKEVICH
Keyword(s):  
Sodium Hydride ◽  
Nucleophilic Agent ◽  
New Synthesis

scholarly journals Hybrid super electron donors – preparation and reactivity

2012 ◽  
Vol 8 ◽  
pp. 994-1002 ◽  
Author(s):  
Jean Garnier ◽  
Douglas W Thomson ◽  
Shengze Zhou ◽  
Phillip I Jolly ◽  
Leonard E A Berlouis ◽  
...  
Keyword(s):  
Room Temperature ◽  
Sodium Hydride ◽  
Electron Donors ◽  
Transfer Reactions ◽  
Aryl Radical ◽  
Selective Effect ◽  
Aryl Radicals ◽  
Organic Electron ◽  
Show Evidence ◽  
Excess Sodium

Neutral organic electron donors, featuring pyridinylidene–imidazolylidene, pyridinylidene–benzimidazolylidene and imidazolylidene–benzimidazolylidene linkages are reported. The pyridinylidene–benzimidazolylidene and imidazolylidene–benzimidazolylidene hybrid systems were designed to be the first super electron donors to convert iodoarenes to aryl radicals at room temperature, and indeed both show evidence for significant aryl radical formation at room temperature. The stronger pyridinylidene–imidazolylidene donor converts iodoarenes to aryl anions efficiently under appropriate conditions (3 equiv of donor). The presence of excess sodium hydride base has a very important and selective effect on some of these electron-transfer reactions, and a rationale for this is proposed.

C-Aroylations of imides and N-aroylations of β-keto amides with aromatic esters by means of sodium hydride to form β-keto imides

1968 ◽  
Vol 46 (15) ◽  
pp. 2561-2566 ◽  
Author(s):  
James F. Wolfe ◽  
George B. Trimitsis ◽  
Charles R. Hauser
Keyword(s):  
Liquid Ammonia ◽  
Sodium Hydride ◽  
Amide Group ◽  
Methyl Groups ◽  
Aromatic Esters ◽  
Synthetic Utility ◽  
C And N ◽  
Hydride Method ◽  
Better Than

Aroylations at the methyl groups of N-acetylbenzamide and p-benzoylaminoacetophenone, and at a methylene position of succinimide with appropriate aromatic esters were effected by means of sodium hydride in refluxing monoglyme. Benzoylation at the amide group of α-benzoylacetamide and salicylamide were accomplished similarly. The yields of β-keto imides from these C- and N-aroylations by sodium hydride, with which intermediate dianions were evidently not formed, were generally much better than those obtained through dianions produced by means of an alkali amide in liquid ammonia. The synthetic utility of the sodium hydride method is discussed.

Tandem Carbon-Radical Peroxidation−Addition to Carbonyl Groups Reaction. A New Synthesis of Steroidal β-Peroxy Lactones

1996 ◽  
Vol 61 (26) ◽  
pp. 9635-9635
Author(s):  
Alicia Boto ◽  
Rosendo Hernández ◽  
Ernesto Suárez ◽  
Carmen Betancor ◽  
María S. Rodríguez
Keyword(s):  
Carbonyl Groups ◽  
New Synthesis

1,3-Selenaphospholes: A New Synthesis from 1,2,3-Selenadiazoles and Kinetically Stabilized Phosphaalkynes1

Synlett ◽  
1991 ◽  
Vol 1991 (04) ◽  
pp. 356-358 ◽  
Author(s):  
Bernd Burkhart ◽  
Steffen Krill ◽  
Yoshinori Okano ◽  
Wataru Ando ◽  
Manfred Regitz
Keyword(s):  
New Synthesis

A New Synthesis and Analysis of Silica Nanowire Periodically Wrapped by Nano-spheres

2016 ◽  
Vol 31 (5) ◽  
pp. 523
Author(s):  
MA Hong-Bing ◽  
BAI Hua ◽  
XUE Chen ◽  
TAO Peng-Fei ◽  
XU Qun-Feng ◽  
...  
Keyword(s):  
New Synthesis
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