Solvent-Free Synthesis of Diazocine

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3471-3475 ◽  
Author(s):  
Widukind Moormann ◽  
Daniel Langbehn ◽  
Rainer Herges
Keyword(s):  
Solvent Free ◽  
Second Step ◽  
Oxidative Dimerization ◽  
Reaction Conditions ◽  
Reducing Conditions ◽  
Lead Powder ◽  
Potential Applications ◽  
The Stability ◽  
Solvent Free Synthesis ◽  
Solvent Free Reaction

A convenient two-step synthesis of diazocine starting from 2-nitrotoluene is described. The first step, the oxidative dimerization of 2-nitrotoluene, is improved to 95% yield. The second step, the reductive azo cyclization, is performed as a solvent-free reaction with lead powder in a ball mill (51% yield). As a reference, the previously described azo cyclization with Zn/Ba(OH)2 is investigated in detail. The results explain why in previous experiments the yields are low and extremely dependent on the reaction conditions. In view of potential applications in photopharmacology, we checked the stability under reducing conditions. Diazocine does not react with glutathione, indicating intracellular stability.

Solvent-free Synthesis of Novel Spirocyclic Oxindole Derivatives via a Michael-Aldol Cascade by Grinding

2018 ◽  
Vol 42 (5) ◽  
pp. 244-246 ◽  
Author(s):  
Renzhi Liu ◽  
Qihong Mei ◽  
Yan Shen ◽  
Yiqiang Wu ◽  
Wenlin Xie
Keyword(s):  
Infrared Spectroscopy ◽  
Solvent Free ◽  
Reaction Conditions ◽  
Novel Synthesis ◽  
Spirocyclic Oxindole ◽  
Solvent Free Synthesis ◽  
Solvent Free Reaction

A simple and novel synthesis of spirocyclic oxindole derivatives by the reaction of ( E)-3-arylideneindole-2-ones and 1,4-dithiane-2,5-diol via a Michael-aldol cascade under solvent-free reaction conditions is reported. This method provides a new practical and facile approach to 4′-hydroxy-2′-aryl-4’,5′-dihydro-2' H-spiro[oxindole-3,3′-thiophen]-2-ones in moderate to good yields. The structures of all the products were characterised by NMR, infrared spectroscopy and HRMS.

Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions

Tetrahedron ◽  
2008 ◽  
Vol 64 (22) ◽  
pp. 5191-5199 ◽  
Author(s):  
Igor Pravst ◽  
Marko Zupan ◽  
Stojan Stavber
Keyword(s):  
Solvent Free ◽  
Reaction Conditions ◽  
Solvent Free Reaction

scholarly journals Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

2013 ◽  
Vol 9 ◽  
pp. 2344-2353 ◽  
Author(s):  
Sudipta Pathak ◽  
Kamalesh Debnath ◽  
Animesh Pramanik
Keyword(s):  
Sulfuric Acid ◽  
Low Cost ◽  
Solvent Free ◽  
Primary Amines ◽  
Solid Catalyst ◽  
Silica Sulfuric Acid ◽  
Reaction Conditions ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Solvent Free Reaction

A convenient and efficient methodology for the synthesis of densely substituted pyrrole-fused isocoumarins, which employs solid-supported silica sulfuric acid (SSA) as catalyst, has been developed. When the mixture of ninhydrin adducts of acetylacetone/ethyl acetoacetate and primary amines was heated on the solid surface of SSA under solvent-free conditions, the pyrrole-fused isocoumarins were formed in good yields. This synthetic method has several advantages such as the employment of solvent-free reaction conditions without the use of any toxic reagents and metal catalysts, the ease of product isolation, the use of a recyclable catalyst, the low cost, the easy availability of the starting materials, and the excellent yields of products.

Biocatalytic and solvent-free synthesis of a bio-based biscyclocarbonate

2018 ◽  
Vol 20 (20) ◽  
pp. 4738-4745 ◽  
Author(s):  
D. S. Wunschik ◽  
K. N. Ingenbosch ◽  
M. Zähres ◽  
J. Horst ◽  
C. Mayer ◽  
...  
Keyword(s):  
Solvent Free ◽  
Reaction Conditions ◽  
Sustainable Resources ◽  
One Step ◽  
Solvent Free Synthesis

An enzymatically controlled one-step synthesis of a non-isocyanate polyurethane monomer from sustainable resources is feasible under mild reaction conditions.

scholarly journals N-Halosuccinimides as Precatalysts for C-, N-, O-, and X-Nucleophilic Substitution Reactions of Alcohols under Mild Reaction Conditions

Catalysts ◽  
2020 ◽  
Vol 10 (4) ◽  
pp. 460
Author(s):  
Njomza Ajvazi ◽  
Stojan Stavber
Keyword(s):  
Nucleophilic Substitution ◽  
Substrate Concentration ◽  
Solvent Free ◽  
Substitution Reactions ◽  
High Substrate Concentration ◽  
Reaction Conditions ◽  
High Substrate ◽  
Nucleophilic Substitution Reactions ◽  
Solvent Free Reaction

N-halosuccinimides (chloro, bromo, and iodo, respectively) were introduced, tested, and applied as efficient and non-metal precatalysts for C-, N-, O-, and X-nucleophilic substitution reactions of alcohols under solvent-free reaction conditions (SFRC) or under high substrate concentration reaction conditions (HCRC) efficiently and selectively, into the corresponding products.

scholarly journals Cyanuric Chloride-Catalyzed Michael Addition of Indoles to Nitroolefins under Solvent-Free Conditions

2013 ◽  
Vol 2013 ◽  
pp. 1-5
Author(s):  
Xiao Juan Yang ◽  
Yun Jing
Keyword(s):  
Michael Addition ◽  
Present Method ◽  
Solvent Free ◽  
Cyanuric Chloride ◽  
Reaction Conditions ◽  
Experimental Procedure ◽  
Solvent Free Conditions ◽  
Short Period ◽  
The Michael Addition ◽  
Solvent Free Reaction

Cyanuric chloride is an inexpensive, efficient, and mild catalyst for the Michael addition of indoles to nitroolefins at 70°C under solvent-free conditions. The simple experimental procedure, solvent-free reaction conditions, utilization of an inexpensive and readily available catalyst, short period of conversion, and excellent yields are the advantages of the present method.

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