Uncatalyzed diastereoselective synthesis of alkyliminofurochromone-derived benzylmalononitriles via a three-component cascade reaction: competition between Diels–Alder cycloaddition and Michael addition

2021 ◽  
Author(s):  
Mohammad Bagher Teimouri ◽  
Zahra Mokhtare ◽  
Hamid Reza Khavasi
Keyword(s):  
Michael Addition ◽  
Heterocyclic Ring ◽  
Cascade Reaction ◽  
Diels Alder ◽  
Chemical Bonds ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
One Pot

Three new chemical bonds and three stereogenic centres and one heterocyclic ring were assembled stereoselectively in a convenient high atom-economy one-pot operation.

Asymmetric Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes

Synthesis ◽  
2017 ◽  
Vol 49 (14) ◽  
pp. 3118-3125 ◽  
Author(s):  
Margus Lopp ◽  
Gert Preegel ◽  
Estelle Silm ◽  
Sandra Kaabel ◽  
Ivar Järving ◽  
...  
Keyword(s):  
Michael Addition ◽  
Cascade Reaction ◽  
One Pot ◽  
Unsaturated Aldehydes ◽  
Michael Acceptors

An asymmetric organocatalytic Michael addition–cyclization cascade reaction has been developed using cyclopentane-1,2-dione as a Michael donor and α,β-unsaturated aldehydes as Michael acceptors. Bicyclic hemiacetals were obtained in excellent yields and enantioselectivities. On the basis of the results, a one-pot reaction has been developed to obtain chiral 3-substituted cyclopentane-1,2-diones and substituted dihydropyrans in good yields and excellent enantioselectivity.

scholarly journals Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes

2021 ◽  
Vol 9 ◽  
Author(s):  
Taiwei Dong ◽  
Peifeng Wei ◽  
Min Li ◽  
Feng Gao ◽  
Yuan Qin
Keyword(s):  
Biologically Active ◽  
Structural Motif ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
Quinone Methides ◽  
One Pot ◽  
Reaction Performance ◽  
High Yields ◽  
Active Natural

As a privileged structural motif, tetrahydroquinoline skeletons widely exist in biologically active natural products and pharmaceuticals. In this protocol, a highly diastereoselective [4 + 2] annulation of ortho-tosylaminophenyl-substituted p-QMs and cyanoalkenes to construct tetrahydroquinoline derivatives has been successfully achieved. This strategy proceeds efficiently under mild condition, offering straightforward route to a variety of 4-aryl-substituted tetrahydroquinolines with high yields, excellent diastereoselectivities, broad functional group tolerance as well as gram-scale capacity. Moreover, a one-pot reaction sequence utilizing in situ generated p-QMs under the similar condition to build tetrahydroquinoline framework is smoothly conducted with good reaction performance as well as step and atom economy.

Solvent free one-pot multi-component synthesis of β-azaarene substituted ketones via a Sn-catalyzed C(sp3)–H functionalization of 2-alkylazaarenes

RSC Advances ◽  
2015 ◽  
Vol 5 (125) ◽  
pp. 103091-103094 ◽  
Author(s):  
Santosh S. Chavan ◽  
Mohsinkhan Y. Pathan ◽  
Shafeek A. R. Mulla
Keyword(s):  
Michael Addition ◽  
Cascade Reaction ◽  
Solvent Free ◽  
Efficient Synthesis ◽  
One Pot

A tin-catalyzed solvent free one-pot multi-component cascade reaction strategy for the efficient synthesis of β-azaarene substituted ketones via an aldol–Michael addition/C(sp3)–H functionalization of 2-alkylazaarenes has been developed.

One-pot synthesis of β-lactams by the Ugi and Michael addition cascade reaction

2018 ◽  
Vol 16 (33) ◽  
pp. 6096-6105 ◽  
Author(s):  
Xing Gao ◽  
Chunhui Shan ◽  
Zhihao Chen ◽  
Yan Liu ◽  
Xia Zhao ◽  
...  
Keyword(s):  
Michael Addition ◽  
Michael Reaction ◽  
Cascade Reaction ◽  
One Pot ◽  
Diversity Oriented Synthesis ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Reaction Cascades

A diversity-oriented synthesis of β-lactams via Ugi/Michael reaction cascades under mild conditions was achieved.

scholarly journals Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4976
Author(s):  
Marie Ruch ◽  
Nicolas Brach ◽  
Roméric Galéa ◽  
Patrick Wagner ◽  
Gaëlle Blond
Keyword(s):  
Cascade Reaction ◽  
Diels Alder ◽  
Domino Reaction ◽  
Efficient Synthesis ◽  
One Pot ◽  
Quaternary Center ◽  
Stereogenic Centers

We report herein an efficient synthesis of furopyran derivatives through a gold(I)-catalyzed domino reaction. The cascade reaction starts with two regioselective cyclizations, a 5-endo-dig and a 8-endo-dig, followed with a Grob-type fragmentation and a hetero Diels–Alder. The obtained furopyran derivatives contain fused and spiro-heterocycles. During this one-pot process, four bonds and four controlled stereogenic centers including a quaternary center are formed.

Isocyanide-Based MCRs: Straightforward Access to Perfluroalkyl­ated γ-Spiroiminolactones

Synthesis ◽  
2018 ◽  
Vol 50 (20) ◽  
pp. 4104-4112 ◽  
Author(s):  
Hui Zhang ◽  
Weiguo Cao ◽  
Lili Tao ◽  
Zhenhua Fan ◽  
Xin Peng ◽  
...  
Keyword(s):  
Michael Addition ◽  
Nucleophilic Addition ◽  
Simple Procedure ◽  
Reaction Times ◽  
Cascade Reaction ◽  
One Pot ◽  
Excellent Chemical

A variety of perfluoroalkyl-substituted γ-spiroiminolactones have been synthesized via a one-pot, three-component cascade reaction in which isocyanides, methyl perfluoroalk-2-ynoates and 1,2-diketones undergo highly regioselective Michael addition, nucleophilic addition and cyclization. This reaction has the advantages of good to excellent chemical yields, operationally simple procedure, and short reaction times.

Diastereoselective synthesis of functionalised carbazoles via a sequential Diels–Alder/ene reaction strategy

RSC Advances ◽  
2015 ◽  
Vol 5 (21) ◽  
pp. 16125-16152 ◽  
Author(s):  
Joseph Cowell ◽  
Matokah Abualnaja ◽  
Stephanie Morton ◽  
Ruth Linder ◽  
Faye Buckingham ◽  
...  
Keyword(s):  
Diels Alder ◽  
Diastereoselective Synthesis ◽  
Reaction Sequence ◽  
One Pot ◽  
Ene Reaction

A one-pot, three-component, synthesis of saturated carbazoles and related pyridazino[3,4-b]indoles is described, involving an intermolecular Diels–Alder/intermolecular ene reaction sequence with relative stereocontrol of up to four stereocentres.

An environmentally benign double Michael addition reaction of heterocyclic ketene aminals with quinone monoketals for diastereoselective synthesis of highly functionalized morphan derivatives in water

2017 ◽  
Vol 19 (15) ◽  
pp. 3574-3584 ◽  
Author(s):  
Yu-Lu Ma ◽  
Kai-Min Wang ◽  
Rong Huang ◽  
Jun Lin ◽  
Sheng-Jiao Yan
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Environmentally Benign ◽  
Diastereoselective Synthesis ◽  
Michael Addition Reaction ◽  
One Pot ◽  
Ketene Aminals

This effort involved an efficient and concise one-pot procedure for the synthesis of morphans based on quinone monoketals 1 reacting with HKAs 2.

Sign in / Sign up

Export Citation Format

Share Document