Diversity oriented, efficient and sustainable synthetic protocol for the synthesis of structurally diverse drug-like complex heterocycles, incorporating privileged heterocyclic systems

2014 ◽  
Vol 1 (1) ◽  
Author(s):  
Sarita Khandelwal ◽  
Anshu Rajawat ◽  
Yogesh Kumar Tailor ◽  
Hemant Kumar Jain ◽  
Mahendra Kumar
Keyword(s):  
Carbonyl Compounds ◽  
Structural Complexity ◽  
Sulfamic Acid ◽  
Acid Catalyst ◽  
Catalytic Amount ◽  
Domino Reaction ◽  
Synthetic Strategy

AbstractA diversity oriented, efficient and sustainable synthetic protocol has been presented for the synthesis of structurally diverse drug-like small heterocycles with structural complexity. The present synthetic strategy involves a three-component domino reaction of 2-aminobenzothiazoles, thiophene-2-carbaldehyde and carbonyl compounds in the presence of a catalytic amount of sulfamic acid as a recyclable ecofriendly acid catalyst.

Zinc Sulfamate Catalyzed Efficient Selective Synthesis of Benzimidazole Derivatives under Ambient Conditions

2019 ◽  
Vol 16 (9) ◽  
pp. 740-749
Author(s):  
Sushil R. Mathapati ◽  
Arvind H. Jadhav ◽  
Mantosh B. Swami ◽  
Jairaj K. Dawle
Keyword(s):  
Benzimidazole Derivative ◽  
Sulfamic Acid ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Product Yield ◽  
Lewis Acidity ◽  
Benzimidazole Derivatives ◽  
Ambient Conditions ◽  
Reaction Condition ◽  
Green Approach

Zinc sulfamate (Zn(NH2SO3)2 is a derivative of sulfamic acid (H3NSO3) which possesses “Lewis acidity” and finds well suited in a number of catalytic applications. The present paper describes an efficient, eco-friendly, and clean synthesis of 2-substituted benzimidazole derivatives by reacting diverse o-phenylenediamine with various substituted aromatic aldehydes using a catalytic amount of zinc sulfamate in ethanol at ambient temperature. As a result, 10 mol.% of Zinc sulfamate catalyst showed 92% of respective product yield with 100% conversion using short reaction period in ethanol. Meanwhile, effect of reaction parameters, such as amount of catalyst, different solvents, and reaction temperature on reaction product, was also studied. In addition, in the optimized reaction condition various substituted biological important benzimidazoles derivatives were prepared by using optimized reaction condition in good to efficient yield. In addition, possible reaction mechanism in the presence of zinc sulfamate for the preparation of benzimidazole derivative was sketched and discussed. The present green approach showed significances with faster reaction rate with inexpensive catalyst, which showed excellent and clean yield of benzimidazole in mild reaction condition with easy work-up procedure.

The synthesis of indeno[de]isochromene derivatives from arylvinyl epoxides and carbonyl compounds via tandem Nazarov and oxa-Pictet–Spengler cyclizations

2021 ◽  
Author(s):  
Nagam Satish ◽  
Siruvuri Krishnam Raju ◽  
Jagadeesh Babu Nanubolu ◽  
Gangarajula Sudhakar
Keyword(s):  
Carbonyl Compounds ◽  
Catalytic Amount

The conversion of aryl vinyl epoxides and carbonyl compounds in the presence of a catalytic amount of BF3·OEt2 to indeno[de]isochromenes via tandem Nazarov and oxa-Pictet–Spengler cyclizations is described.

scholarly journals Ru-NHC Catalyzed Domino Reaction of Carbonyl Compounds and Alcohols: A Short Synthesis of Donaxaridine

ACS Omega ◽  
2017 ◽  
Vol 2 (11) ◽  
pp. 8234-8252 ◽  
Author(s):  
Girish Singh Bisht ◽  
Moreshwar Bhagwan Chaudhari ◽  
Vruta Sunil Gupte ◽  
Boopathy Gnanaprakasam
Keyword(s):  
Carbonyl Compounds ◽  
Domino Reaction ◽  
Short Synthesis

scholarly journals Metal-Free Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups

2021 ◽  
Author(s):  
Benedikt Grau ◽  
Maximilian Dill ◽  
Frank Hampel ◽  
Axel Kahnt ◽  
Norbert Jux ◽  
...  
Keyword(s):  
Liquid Crystalline ◽  
Diels Alder ◽  
Domino Reaction ◽  
Aromatic Rings ◽  
Light Emitting ◽  
Crystalline Materials ◽  
Metal Free ◽  
Synthetic Strategy ◽  
Starting Compound ◽  
Liquid Crystalline Materials

Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, redox materials, organic light-emitting diodes and photochemical switches. Statistical synthesis of simple symmetrical HABs is known <i>via</i> low-yielding cyclotrimerization or Diels-Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB <i>via</i> an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and <i>α,α</i>-dicyanoolefins as easily available starting materials. Resulting domino product – functionalized triarylbenzene (TAB) - can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to creating diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.

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