An efficient synthesis of 2-amino-4-aryl-6,7,8,9-tetrahydro-5H-benzo[7]annulene-1,3-dicarbonitriles in THF with DBU as catalyst

Rong, Liangce; Tao, Shimin; Sheng, Xia; Liu, Lihua; Yin, Shou-Wei; Shi, Yanhui

doi:10.1007/s11164-012-0491-3

Cited by 8 publications

(3 citation statements)

References 15 publications

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“…For example, the one‐pot synthesis of 2‐amino‐4‐aryl‐6,7,8,9‐tetrahydro‐5 H ‐benzo[7]annulene‐1,3‐dicarbonitriles 197 from cycloheptanone ( 194 ), aromatic aldehydes 195 , and malononitrile ( 196 ) in THF was reported by Rong et al. (Scheme ) . These substrates acted as typical acceptor–donor–acceptor (A–D–A) moieties.…”

Section: Dbu‐mediated Benzannulation Reactionsmentioning

confidence: 99%

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

et al. 2018

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Benzene and itsderivativesare the most abundant substructures of several interesting classes of compound, such as bioactive molecules. Owing to their importance, the development of methods for their constructionh as attracted considerable attention.H owever,t he regioselectives ynthesis of polysubstituted aromatic and heteroaromatic compounds by using aromatic substitution is challenging, because it provides derivatives with restricted substitution patterns. Therefore, the benzannulation reaction-the assembly of benzene derivatives from acyclicp recursors-constitutes as uperior and highly versatile approach to polysubstituted aromatic and heteroaromatic compounds,a nd variouse fficient benzannulation reactions have been reported.R epresentative examples include Cs 2 CO 3 , t-BuOK,a nd DBU-catalyzed reactions for the construction of valuableb enzene derivatives. The central objective of this Focus Review is to highlight base-mediated benzannulation reactions under transitionmetal-free conditions for the construction of aromatic and heteroaromatic compounds.[a] Dr.Recently,P an and co-workers investigated the K 2 CO 3 -catalyzed cascade benzannulation reaction of b-keto sulfones 1 with acetylene ketones 2 by using 30 %m ol K 2 CO 3 without other additives,w hich afforded new sulfonylbenzene derivatives 3 in good yields through ab enzannulation reaction (Scheme 1a). [18] Av ariety of electron-donating ande lectron-withdrawing groups were well-tolerated under the optimized reaction conditions. The proposed reactionpathway proceeded through se-quentialM ichael addition, intramolecular cyclization, hydrogen abstraction, and dehydration reactions (Scheme 1b).Scheme55. Synthesis of unsymmetrical biaryls from the annulation/aromatizationr eactionsof1 ,4-pentanedienes with nitroalkanes.Scheme56. DBU-promoted [5+ +1] annulation reaction of a-alkenoyl ketene-S,S-acetalswith nitroalkanes.

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Section: Dbu‐mediated Benzannulation Reactionsmentioning

confidence: 99%

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

et al. 2018

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“…L. Rong et al, have synthesized 2-amino-4aryl-6,7,8,9-tetrahydro-5H-benzo [7] annulene-1,3-dicarbonitriles using THF as a solvent and DBU as a catalyst, which consumed 2 h of time in reflux conditions. [33] Pagadala et al, utilized water as a solvent with a Zn-VCO 3 catalyst for multifunctionalized benzene derivative preparation and obtained the products in 2 h in a reflux setup at 80 °C. [34] Though the product yield is appreciated in both methods, it is better to avoid organic solvents in concern with ecofriendly conditions, the consumption of electrical energy, and the reduction of reaction time.…”

Section: Introductionmentioning

confidence: 99%

“…The earlier research on this type of core structure construction involved the usage of organic solvents, catalysts, traditional methodologies, tedious and expensive. L. Rong et al ., have synthesized 2‐amino‐4‐aryl‐6,7,8,9‐tetrahydro‐5H‐benzo [7] annulene‐1,3‐dicarbonitriles using THF as a solvent and DBU as a catalyst, which consumed 2 h of time in reflux conditions [33] . Pagadala et al., utilized water as a solvent with a Zn‐VCO 3 catalyst for multifunctionalized benzene derivative preparation and obtained the products in 2 h in a reflux setup at 80 °C [34] .…”

Section: Introductionmentioning

confidence: 99%

A New and an Eco‐Friendly Approach for the Construction of Multi‐Functionalized Benzenes with Computational Studies

Damera¹,

Pagadala²

2023

Chemistry & Biodiversity

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The new path chosen is more appropriate in the context of green chemistry. This research aims to construct 5,6,7,8-tetrahydronaphthalene-1,3-dicarbonitrile (THNDC) and 1,2,3,4-tetrahydroisoquinoline-6,8-dicarbonitrile (THIDC) derivatives via the cyclization of three easily obtainable reactants under an environmentally benign mortar and pestle grinding technique. Notably, the robust route offers an esteemed opportunity for the introduction of multi-substituted benzenes and ensures the good compatibility of bioactive molecules. Furthermore, the synthesized compounds are investigated using docking simulations with two representative drugs (6c and 6e) for target validation. The physicochemical, pharmacokinetic, drug-like properties (ADMET), and therapeutic friendliness characteristics of these synthesized compounds are computed.

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Lipase from Porcine Pancreas: An Efficient Biocatalyst for the Synthesis of ortho‐Aminocarbonitriles

et al. 2018

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Enzymatic processes are highly specific, green, operate at mild conditions and reduce environmental pollution in comparison to conventional hazardous chemical processes. Herein, we describe a new strategy for the synthesis of ortho‐aminocarbonitriles by a multicomponent reaction of aromatic aldehydes, cyclohexanone and two equivalents of malononitrile at 40 °C. A new six‐membered ring was constructed by breaking seven bonds while four new bonds were formed. The solvent, lipase quantity and reaction conditions were optimized. The advantages of this biocatalyst mediated synthesis of ortho‐aminocarbonitriles comprised a one‐pot procedure with simple operations and higher yields, which were reported for the first time by biocatalysis.

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An efficient synthesis of 2-amino-4-aryl-6,7,8,9-tetrahydro-5H-benzo[7]annulene-1,3-dicarbonitriles in THF with DBU as catalyst

Cited by 8 publications

References 15 publications

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

A New and an Eco‐Friendly Approach for the Construction of Multi‐Functionalized Benzenes with Computational Studies

Lipase from Porcine Pancreas: An Efficient Biocatalyst for the Synthesis of ortho‐Aminocarbonitriles

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