Enantio- and diastereoselective synthesis of spiropyrazolones via an organocatalytic [1 + 2 + 3] multicomponent reaction

2019 ◽  
Vol 17 (41) ◽  
pp. 9217-9225 ◽  
Author(s):  
Yan-Ling Ji ◽  
He-Ping Li ◽  
Yue-Yan Ai ◽  
Guo Li ◽  
Xiang-Hong He ◽  
...  
Keyword(s):  
Multicomponent Reaction ◽  
Diastereoselective Synthesis ◽  
Asymmetric Catalytic ◽  
High Yields

An asymmetric catalytic [1 + 2 + 3] multicomponent reaction of malononitrile, benzaldehyde and α-arylidene pyrazolinones to produce spiropyrazolones in high yields, with excellent enantioselectivities and good diastereoselectivities.

scholarly journals Electrochemical multicomponent synthesis of 4-selanylpyrazoles under catalyst- and chemical-oxidant-free conditions

2021 ◽  
Author(s):  
Yan Wu ◽  
Jin-Yang Chen ◽  
Jing Ning ◽  
Xue Jiang ◽  
Jie Deng ◽  
...  
Keyword(s):  
Multicomponent Reaction ◽  
Raw Materials ◽  
Multicomponent Synthesis ◽  
Mild Conditions ◽  
Simple Protocol ◽  
High Yields

An electrochemical multicomponent reaction was established under catalyst-, chemical-oxidant-free and mild conditions, which provides an eco-friendly and simple protocol for constructing 4-selanylpyrazoles from easily available raw materials with high yields.

A facile approach for the synthesis of 1,3-di- and 1,2,3-tri-substituted indolizines

2015 ◽  
Vol 93 (5) ◽  
pp. 542-545 ◽  
Author(s):  
Jun Tan ◽  
Yiwen Yang ◽  
Jie Chen ◽  
Chunxiang Kuang
Keyword(s):  
Multicomponent Reaction ◽  
Pyridinium Salt ◽  
Quinolinium Salt ◽  
Convenient Synthesis ◽  
High Yields

A convenient synthesis of 1,3-di- and 1,2,3-tri-substituted indolizines involving the multicomponent reaction of pyridinium salt (or quinolinium salt), olefine acid, and 1,2-dichloroethane has been achieved. The process proceeds smoothly in moderate to high yields.

scholarly journals Diastereoselective Synthesis of Cyclopenta[c]furans by a Catalytic Multicomponent Reaction

2016 ◽  
Vol 128 (39) ◽  
pp. 12042-12045 ◽  
Author(s):  
Stalin R. Pathipati ◽  
Angela van der Werf ◽  
Lars Eriksson ◽  
Nicklas Selander
Keyword(s):  
Multicomponent Reaction ◽  
Diastereoselective Synthesis

One-pot multicomponent synthesis of β-acetamidoketones catalysed by pTSA1

2007 ◽  
Vol 85 (7-8) ◽  
pp. 479-482 ◽  
Author(s):  
Biswanath Das ◽  
Kongara Ravinder Reddy ◽  
Yallamalla Srinivas ◽  
Rathod Aravind Kumar
Keyword(s):  
Multicomponent Reaction ◽  
Acetyl Chloride ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
High Yields ◽  
Three Component Coupling

A catalytic amount of pTSA has been found to be effective to carry out a one-pot three-component coupling of aromatic aldehydes, enolizable ketones or ketoesters, and acetonitrile in the presence of acetyl chloride to afford β-acetamidoketones in high yields. Short reaction times and inexpensive catalyst are main advantages of this protocol.Key words: β-acetamidoketone, pTSA, multicomponent reaction, diastereoselectivity.

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.

Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols

2018 ◽  
Vol 21 (2) ◽  
pp. 476-480 ◽  
Author(s):  
Yoshikazu Horino ◽  
Miki Murakami ◽  
Ataru Aimono ◽  
Jun Hee Lee ◽  
Hitoshi Abe
Keyword(s):  
Multicomponent Reaction ◽  
Diastereoselective Synthesis ◽  
Homoallylic Alcohols

Diastereoselective Synthesis of Spiro[carbazole-3,5'-pyrimidines] and Spiro[carbazole-3,1'-cyclohexanes] via Four-component Reaction

2021 ◽  
Author(s):  
Shao-Cong Zhan ◽  
Ren-Jie Fang ◽  
Jing Sun ◽  
Chaoguo Yan
Keyword(s):  
Aromatic Aldehyde ◽  
Multicomponent Reaction ◽  
Diastereoselective Synthesis

The functionalized spiro[carbazole-3,5'-pyrimidines] and spiro[carbazole-3,1'-cyclohexanes] were efficiently synthesized in satisfactory yields with high diastereoselectivity by CuSO4 catalyzed multicomponent reaction of indole-2-acetate, aromatic aldehyde and 1,3-dimethylbarbituric acid or dimedone. The reaction...

Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 267-271 ◽  
Author(s):  
Firouz Matloubi Moghaddam ◽  
Atiyeh Moafi ◽  
Behzad Jafari ◽  
Alexander Vilinger ◽  
Peter Langer
Keyword(s):  
Cycloaddition Reaction ◽  
Reaction Times ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
One Pot ◽  
Three Component Reaction ◽  
Relative Stereochemistry ◽  
High Yields

A regio- and diastereoselective synthesis of 2,3-dihydro-10b′H-spiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N-ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

An efficient catalyst-free chemoselective multicomponent reaction for the synthesis of pyrimidine functionalized pyrrolo-annelated derivatives

RSC Advances ◽  
2015 ◽  
Vol 5 (31) ◽  
pp. 24327-24335 ◽  
Author(s):  
Yuvaraj Dommaraju ◽  
Somadrita Borthakur ◽  
Nimmakuri Rajesh ◽  
Dipak Prajapati
Keyword(s):  
Multicomponent Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
Efficient Catalyst ◽  
Catalyst Free ◽  
High Yields

An efficient catalyst-free, one-pot multicomponent reaction has been developed for the synthesis of pyrimidine functionalized pyrrolo-annelated derivatives. The method offers easy and column free separation, mild reaction conditions and high yields.

scholarly journals The Pictet-Spengler Reaction Updates Its Habits

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 414 ◽  
Author(s):  
Andrea Calcaterra ◽  
Laura Mangiardi ◽  
Giuliano Delle Monache ◽  
Deborah Quaglio ◽  
Silvia Balducci ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Synthetic Method ◽  
Ring Closing Metathesis ◽  
Phase Synthesis ◽  
Acid Catalyzed ◽  
High Yields

The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations.

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