An Exploration of Organocatalyst 1,4-Diazabicyclo[2.2.2]octane in the Direct Regioselective and Chemoselective γ-Addition of β-Keto Amide on Isatin to Afford Structurally Diverse Molecular Frameworks

2015 ◽  
Vol 68 (3) ◽  
pp. 453 ◽  
Author(s):  
Pramod B. Thakur ◽  
Harshadas M. Meshram
Keyword(s):  
Environmentally Benign ◽  
Direct Access ◽  
Metal Free ◽  
Structural Framework ◽  
High Yields

An efficient protocol promoted by 1,4‐diazabicyclo[2.2.2]octane is described for the regioselective and chemoselective γ-addition of β-keto amides on isatins to afford γ-(3-hydroxy-2-oxindole)-β-keto amide structural framework under metal-free conditions. The developed method is mild, generates high yields, and is applicable for a variety of isatin electrophiles as well as β-keto amides. Moreover, the procedure is very handy and environmentally benign in nature, and provides direct access for the synthesis of diverse functionalized 3-β-keto amide-substituted 3-hydroxy-2-oxindole structural scaffolds from readily available starting materials.

Metal-free [3+3] benzannulation of 1-indanylidene-malononitrile with Morita–Baylis–Hillman carbonates: direct access to functionalized fluorene and fluorenone derivatives

2020 ◽  
Vol 56 (13) ◽  
pp. 1948-1951 ◽  
Author(s):  
Ya-Sa Xie ◽  
Run-Feng Huang ◽  
Ran Li ◽  
Chuan-Bao Zhang ◽  
Ji-Ya Fu ◽  
...  
Keyword(s):  
Direct Access ◽  
Metal Free ◽  
Wide Range ◽  
High Yields

An efficient [3+3] benzannulation of Morita–Baylis–Hillman carbonates with 1-indanylidenemalononitrile was achieved selectively delivering a wide range of functional fluorene or fluorenone compounds in high yields (up to 86% yields).

scholarly journals Direct access to multi-functionalized benzenes via [4 + 2] annulation of α-cyano-β-methylenones and α,β-unsaturated aldehydes

RSC Advances ◽  
2020 ◽  
Vol 10 (49) ◽  
pp. 29171-29174 ◽  
Author(s):  
Qianfa Jia ◽  
Yunfei Lan ◽  
Xin Ye ◽  
Yinhe Lin ◽  
Qiao Ren
Keyword(s):  
Direct Access ◽  
Reaction Conditions ◽  
Metal Free ◽  
Unsaturated Aldehydes ◽  
Wide Range ◽  
High Yields

An efficient [4 + 2] benzannulation of α-cyano-β-methylenones and α,β-unsaturated aldehydes was achieved under metal-free reaction conditions selectively delivering a wide range of polyfunctional benzenes in high yields respectively (up to 94% yield).

Ultrasound-assisted aqua-mediated synthesis of multi-substituted tetrahydropyridine-3-carboxylates using N-carboxymethyl-3-pyridinium hydrogensulfate ([N-CH2CO2H-3-pic]+HSO4−) as a new efficient ionic liquid catalyst

2021 ◽  
Vol 3 (6) ◽  
Author(s):  
Kobra Nikoofar ◽  
Fatemeh Shahriyari
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
H Nmr ◽  
Sonic Waves ◽  
Ft Ir ◽  
High Yields ◽  
Work Up ◽  
C Nmr

AbstractA simple, straightforward, and ultrasound-promoted method for the preparation of some highly functionalized tetrahydropyridines reported via pseudo five-component reaction of (hetero)aromatic aldehydes, different anilines, and alkyl acetoacetates in the presence of [N-CH2CO2H-3-pic]+HSO4−, as a novel ionic liquid, in green aqueous medium. The IL was synthesized utilizing simple and easily-handled substrates and characterized by FT-IR, 1H NMR, 13C NMR, GC-MASS, FESEM, EDX, and TGA/DTG techniques. The procedure contains some highlighted aspects which are: (a) performing the MCR in the presence of aqua and sonic waves, as two main important and environmentally benign indexes in green and economic chemistry, (b) high yields of products within short reaction times, (c) convenient work-up procedure, (d) preparing the new IL via simple substrates and procedure.

scholarly journals Metal-Free Oxidative Dimerization of Dithiocarbamates: Direct Access to 3,5-Bis-mercapto-1,2,4-thiadiazoles

SynOpen ◽  
2017 ◽  
Vol 01 (01) ◽  
pp. 0138-0142 ◽  
Author(s):  
Azim Halimehjani ◽  
Yazdanbakhsh Nosood ◽  
Shaghayegh Didaran ◽  
Fezzeh Aryanasab
Keyword(s):  
Periodic Acid ◽  
Reaction Times ◽  
Direct Access ◽  
Oxidative Dimerization ◽  
Metal Free

A facile and efficient protocol for the synthesis of 3,5-bis-mercapto-1,2,4-thiadiazoles by the oxidative dimerization of S-alkyl dithiocarbamates using periodic acid as an inexpensive and commercially available oxidant is reported. High to excellent yields and short reaction times are the main advantages of this procedure.

Electrochemical Oxidative Cyclization of Alkenes, Boronic Acids, and Dichalcogenides to Access Chalcogenated Boronic Esters and 1,3-Diols

2021 ◽  
Author(s):  
Changfeng Huang ◽  
Jijing Hu ◽  
Guangxian Chen ◽  
Minjian Wu ◽  
Hua Cao ◽  
...  
Keyword(s):  
Boronic Acids ◽  
Oxidative Cyclization ◽  
Environmentally Benign ◽  
Allylic Alcohols ◽  
Efficient Manner ◽  
Metal Free ◽  
Boronic Esters

A sustainable, environmentally benign electrochemical oxidative three-component cyclization of allylic alcohols, boronic acids, and dichalcogenides under metal-free and oxidant-free conditions has been developed, which provides an efficient manner for the...

scholarly journals A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3031 ◽  
Author(s):  
Xiaodong Tang ◽  
Songlei Zhu ◽  
Ying Ma ◽  
Ren Wen ◽  
Lanqi Cen ◽  
...  
Keyword(s):  
Environmentally Benign ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Dicarbonyl Compounds ◽  
Pyrrole Derivatives ◽  
Three Component Reaction ◽  
High Yields ◽  
Operational Simplicity

A green, convenient and tandem procedure for the efficient synthesis of highly substituted indeno[1,2-b]pyrrole and acenaphtho[1,2-b]pyrrole derivatives by domino three-component reaction of tryptamine/benzylamine, 1,3-dicarbonyl compounds and ninhydrin/ acenaphthenequinone is described. The significant features of this procedure were characterized by mild reaction conditions, high yields, operational simplicity and it being environmentally benign.

Cinchona alkaloid and di-tert-butyldicarbonate–DMAP promoted efficient synthesis of (E)-nitroolefins

RSC Advances ◽  
2016 ◽  
Vol 6 (59) ◽  
pp. 54495-54502 ◽  
Author(s):  
Nataraj Poomathi ◽  
Paramasivan T. Perumal
Keyword(s):  
Cinchona Alkaloid ◽  
Efficient Synthesis ◽  
Metal Free ◽  
High Yields

A simple and efficient metal-free methodology for the synthesis of β-nitroolefins has been developed from arylidinemalononitrile using bifunctional cinchona alkaloid along with di-tert-butyldicarbonate–DMAP in high yields with total selectivity.

A metal-free hydrogenation of 3-substituted 2H-1,4-benzoxazines

2016 ◽  
Vol 14 (34) ◽  
pp. 8026-8029 ◽  
Author(s):  
Simin Wei ◽  
Xiangqing Feng ◽  
Haifeng Du
Keyword(s):  
Metal Free ◽  
High Yields

A metal-free hydrogenation of 3-substituted 2H-1,4-benzoxazines was realized to furnish the desired products in high yields with up to 42% ee.

Synthesis of functionalized 3-isochromanones via metal-free intramolecular alkoxylation-initiated cascade cyclization

2019 ◽  
Vol 21 (11) ◽  
pp. 3023-3028 ◽  
Author(s):  
Ying-Qi Zhang ◽  
Xin-Qi Zhu ◽  
Yin Xu ◽  
Hao-Zhen Bu ◽  
Jia-Le Wang ◽  
...  
Keyword(s):  
Allyl Ether ◽  
Metal Free ◽  
Cascade Cyclization ◽  
High Yields

A metal-free intramolecular alkoxylation-initiated cascade cyclization of allyl ether-tethered ynamides has been developed, leading to functionalized 3-isochromanones in high yields.

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