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.

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.

New efficient synthesis of benzofuro[2,3-b]pyrroles utilizing a reactive nitrilium trapping approach by an acid-promoted cascade addition/cyclization sequence

2020 ◽  
Vol 44 (9) ◽  
pp. 3632-3636
Author(s):  
Sandip Gangadhar Balwe ◽  
Yeon Tae Jeong
Keyword(s):  
Cascade Reaction ◽  
Efficient Synthesis ◽  
One Pot ◽  
Highly Efficient

The first p-TSA·H2O-catalyzed highly efficient one-pot cascade reaction for the synthesis of novel fused tricyclic benzofuro[2,3-b]pyrroles has been discovered.

Visible-Light Photoredox-Catalyzed Cascade Reaction for the Synthesis of Pyrrolo[2,1-a]isoquinoline-Substituted Phosphonates

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 522-529 ◽  
Author(s):  
Deqing Shi ◽  
Lingna Wang ◽  
Tiancong Ma ◽  
Mingming Qiao ◽  
Qiangxian Wu ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Cascade Reaction ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Oxidative Aromatization ◽  
Activated Olefins ◽  
Catalyzed Oxidation

A visible-light photoredox-catalyzed oxidation/[3+2] cycloaddition/oxidative aromatization cascade reaction of [(3,4-dihydroisoquinolin-2(1H)-yl)methyl]phosphonates and activated olefins or alkynes for the efficient synthesis of potentially biological active pyrrolo[2,1-a]isoquinoline-substituted phosphonates was developed. This transformation features mild reaction conditions (i.e., visible light irradiation, room temperature), molecular oxygen (O2) as a green oxidant, simple ‘one-pot’ operation.

scholarly journals Facile synthesis of annulated heterocyclic benzo[kl]acridine derivatives via one-pot N–H/C–H coupling

2016 ◽  
Vol 3 (11) ◽  
pp. 1520-1523 ◽  
Author(s):  
Yulian Zagranyarski ◽  
Artem Skabeev ◽  
Yingjie Ma ◽  
Klaus Müllen ◽  
Chen Li
Keyword(s):  
Domino Reaction ◽  
Efficient Synthesis ◽  
Facile Synthesis ◽  
One Pot ◽  
Acridine Derivatives

A facile and efficient synthesis of benzo[kl]acridines was developed based on a domino reaction via a combinatorial catalyst approach.

scholarly journals Sustainable synthesis of 3-substituted phthalides via a catalytic one-pot cascade strategy from 2-formylbenzoic acid with β-keto acids in glycerol

2017 ◽  
Vol 13 ◽  
pp. 1425-1429 ◽  
Author(s):  
Lina Jia ◽  
Fuzhong Han
Keyword(s):  
Natural Products ◽  
Cascade Reaction ◽  
Catalytic Process ◽  
Efficient Synthesis ◽  
One Pot ◽  
Keto Acids ◽  
Synthesis Strategy ◽  
Therapeutic Activities

Background: Phthalides are privileged constituents of numerous pharmaceuticals, natural products and agrochemicals and exhibit several biological and therapeutic activities. Therefore, the development of new, facile, and sustainable strategies for the construction of these moieties is highly desired. Results: A broad substrate scope for β-keto acids was found to be strongly compatible with this catalytic process, affording a wide variety of 3-substituted phthalides in good to excellent yields. Conclusion: A concise and efficient synthesis strategy of 3-substituted phthalides from 2-formylbenzoic acid and β-keto acids via a catalytic one-pot cascade reaction in glycerol has been accomplished.

An Intramolecular Diels–Alder Furan (IMDAF) Approach towards the Synthesis of Isoindolo[2,1-a]quinazolines and Isoindolo[1,2-b]quinazolines

Synthesis ◽  
2017 ◽  
Vol 49 (16) ◽  
pp. 3749-3767 ◽  
Author(s):  
Vladimir Zaytsev ◽  
Ekaterina Revutskaya ◽  
Tatiana Nikanorova ◽  
Eugeniya Nikitina ◽  
Pavel Dorovatovskii ◽  
...  
Keyword(s):  
Unsaturated Acid ◽  
Nitrogen Heterocycles ◽  
Diels Alder ◽  
Isatoic Anhydride ◽  
One Pot ◽  
Efficient Approach ◽  
Condensation Reactions ◽  
Stereogenic Centers ◽  
Acid Anhydrides

An efficient approach to bridged pentacyclic nitrogen heterocycles via the tandem acylation/intramolecular Diels–Alder furan (IMDAF) reaction of 2-furylquinazolinones is described. Reactions of α,β-unsaturated acid anhydrides with 2-furyl-2,3-dihydroquinazolin-4-ones give 6b,9-epoxyisoindolo[2,1-a]quinazolines in average yields. In this case, the exo-IMDAF reactions proceed with excellent diastereoselectivity giving five stereogenic centers and three new rings in one synthetic step. Isomeric 2,4a-epoxyisoindolo[1,2-b]quinazolines are obtained by one-pot, three-component condensation reactions of allylamine, isatoic anhydride and furaldehydes involving the same IMDAF­ reaction as the key step. Some useful transformations including halogenation, hydrogenation, Prilezhaev epoxidation, and esterification of the synthesized epoxyisoindoloquinazolines are also demonstrated.

Efficient synthesis of pyrrolo[1,2-a]quinoxalines catalyzed by a Brønsted acid through cleavage of C–C bonds

2016 ◽  
Vol 14 (36) ◽  
pp. 8529-8535 ◽  
Author(s):  
Caixia Xie ◽  
Lei Feng ◽  
Wanli Li ◽  
Xiaojun Ma ◽  
Xinkun Ma ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Domino Reaction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Efficient Synthesis ◽  
One Pot ◽  
Keto Esters ◽  
Brönsted Acid

An efficient and convenient one-pot domino reaction for the direct synthesis of pyrrolo[1,2-a]quinoxalines has been developed. β-Diketones and β-keto esters are well tolerated to give the corresponding products in moderate to excellent yields.

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.

Microwave-assisted expeditious and efficient synthesis of novel quinolin-4-ylmethoxychromen-2- and -4-ones catalyzed by YbCl3 under a solvent free one-pot three component domino reaction and their antimicrobial activity

RSC Advances ◽  
2015 ◽  
Vol 5 (113) ◽  
pp. 93067-93080 ◽  
Author(s):  
Sumit Kumar ◽  
Alok Patel ◽  
Naseem Ahmed
Keyword(s):  
Antimicrobial Activity ◽  
Solvent Free ◽  
Domino Reaction ◽  
Efficient Synthesis ◽  
One Pot ◽  
Microwave Assisted ◽  
High Yields

MW assisted multicomponent A3 synthesis was developed for the synthesis of quinolin-4-ylmethoxychromen-2- and -4-ones in high yields with YbCl3 and reused efficiently for four times.

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