Reactions of Active Methylene Compounds with Benzhydrol During Solvolysis in Formic Acid

2003 ◽  
Vol 56 (5) ◽  
pp. 385 ◽  
Author(s):  
Glen C. Gullickson ◽  
David E. Lewis
Keyword(s):  
Formic Acid ◽  
Ritter Reaction ◽  
Reaction Products ◽  
Reaction Conditions ◽  
Active Methylene Compounds ◽  
Active Methylene

Formic acid reacts with benzhydrol to give benzhydryl formate, which reacts with active methylene compounds in refluxing formic acid to give either C-alkylation or Ritter reaction products. The product formed is determined by the equilibrium enol content of the active methylene compound. These reaction conditions avoid the use of halogenated reaction solvents, and the pure products are isolated without recourse to chromatography.

scholarly journals Synthesis of Polyfunctionalized 4H-Pyrans

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Manisha Bihani ◽  
Pranjal P. Bora ◽  
Ghanashyam Bez
Keyword(s):  
Organic Solvents ◽  
Ethyl Acetoacetate ◽  
Room Temperature ◽  
Temperature Reaction ◽  
Chromatographic Purification ◽  
Reaction Conditions ◽  
One Pot ◽  
Experimental Procedure ◽  
Active Methylene Compounds ◽  
Active Methylene

Amberlyst A21 catalyzed one-pot three-component coupling of aldehyde and malononitrile with active methylene compounds such as acetylacetone and ethyl acetoacetate for the synthesis of pharmaceutically important polyfunctionalized 4H-pyrans has been reported. Simple experimental procedure, no chromatographic purification, no hazardous organic solvents, easy recovery and reusability of the catalyst, and room temperature reaction conditions are some of the highlights of this protocol for the synthesis of pharmaceutically relevant focused libraries.

scholarly journals Efficient Knoevenagel Condensation Reactions Catalyzed by Activated Gel Zirconium(IV) Oxide

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Mohammad Reza Poor Heravi ◽  
S. Piri
Keyword(s):  
Knoevenagel Condensation ◽  
Condensation Reaction ◽  
Reaction Conditions ◽  
Condensation Reactions ◽  
Active Methylene Compounds ◽  
Active Methylene

The condensation reaction has been carried out very conveniently to obtain the corresponding substituted 2,2′-(arylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) in excellent yields. The reaction conditions are very mild and applicable to various aldehydes as well as active methylene compounds.

scholarly journals Ammonium Chloride: An Efficient and Environmentally benign Catalyst for Knoevenagel Condensation of Carbonyl and Active Methylene Compounds

2020 ◽  
Vol 32 (12) ◽  
pp. 3024-3028
Author(s):  
S. Tasqeeruddin ◽  
Yahya I. Asiri ◽  
M. Mujahid A lam
Keyword(s):  
Ammonium Chloride ◽  
Large Scale ◽  
Knoevenagel Condensation ◽  
Catalytic Amount ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Active Methylene Compounds ◽  
Characteristic Features ◽  
Active Methylene

In the present study, a rapid, simple and an efficient procedure for the Knoevenagel condensation of various carbonyl and active methylene compounds in ethanol at a moderate temperature in the presence of a catalytic amount of an efficient, environmentally benign and inexpensive ammonium chloride is reported. Simple reaction procedure, economic and ecofriendly catalyst, mild reaction conditions and good to excellent yield of the products are the characteristic features of this study. The non-extractive workup/purification, economic and environmentally benign catalyst make this operationally straightforward procedure affordable for large scale.

Preparation and Reactions of 2-azidoquinoline-3-carboxaldehyde with Primary Amines and Active Methylene Compounds

2009 ◽  
Vol 2009 (4) ◽  
pp. 220-224 ◽  
Author(s):  
Nabila M. Ibrahim ◽  
Hisham Abdallah A. Yosef ◽  
Mohamed Refat H. Mahran
Keyword(s):  
Primary Amines ◽  
Reaction Products ◽  
Spectroscopic Measurements ◽  
Active Methylene Compounds ◽  
Active Methylene

Preparation of 2-azidoquinoline-3-carboxaldehyde has been attempted and its tautomerism has been discussed. The reactivity of 2-azidoquinoline-3-carboxaldehyde towards primary amines, hydrazines and active methylene compounds has been investigated. Analytical and spectroscopic measurements have assisted the assignment of appropriate structures to the new reaction products.

scholarly journals Application of Commercially Available Anhydrous Potassium Fluoride for a Convenient Synthesis of Ketene Dithioacetals

1999 ◽  
Vol 23 (8) ◽  
pp. 492-493
Author(s):  
Sabir H. Mashraqui ◽  
Harini Hariharasubrahmanian
Keyword(s):  
Carbon Disulfide ◽  
Alkylating Agent ◽  
Potassium Fluoride ◽  
Solid Support ◽  
Ambient Conditions ◽  
Ketene Dithioacetals ◽  
Convenient Synthesis ◽  
Active Methylene Compounds ◽  
Active Methylene

Commercially available anhydrous KF without activation or solid support promotes condensation between active methylene compounds, carbon disulfide and an alkylating agent in dry DMF to allow the preparation of a variety of ketene dithioacetals in fair to good yields under ambient conditions.

scholarly journals Prebiotic Route to Thymine from Formamide—A Combined Experimental–Theoretical Study

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2248
Author(s):  
Lukáš Petera ◽  
Klaudia Mrazikova ◽  
Lukas Nejdl ◽  
Kristyna Zemankova ◽  
Marketa Vaculovicova ◽  
...  
Keyword(s):  
Formic Acid ◽  
Quantum Chemical ◽  
Prebiotic Chemistry ◽  
Theoretical Study ◽  
Reaction Pathway ◽  
Hydrolysis Product ◽  
Current Paper ◽  
Reaction Conditions ◽  
Chemical Modeling ◽  
Chemistry Research

Synthesis of RNA nucleobases from formamide is one of the recurring topics of prebiotic chemistry research. Earlier reports suggest that thymine, the substitute for uracil in DNA, may also be synthesized from formamide in the presence of catalysts enabling conversion of formamide to formaldehyde. In the current paper, we show that to a lesser extent conversion of uracil to thymine may occur even in the absence of catalysts. This is enabled by the presence of formic acid in the reaction mixture that forms as the hydrolysis product of formamide. Under the reaction conditions of our study, the disproportionation of formic acid may produce formaldehyde that hydroxymethylates uracil in the first step of the conversion process. The experiments are supplemented by quantum chemical modeling of the reaction pathway, supporting the plausibility of the mechanism suggested by Saladino and coworkers.

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