Multicomponent reaction (MCR) for constructing bis-spirocyclohexane skeletons using β-nitrostyrene derived MBH acetates, 1,3-indanedione and aldehydes via [1 + 1 + 1 + 3] annulation DOI Creative Commons
Veera Babu Gudise, Shaik Anwar

RSC Advances, Journal Year: 2023, Volume and Issue: 13(39), P. 27456 - 27460

Published: Jan. 1, 2023

AB 2 C type four component quadruple cascade reaction between MBH acetate, 1,3-indanedione and aldehydes via [1 + 1 3] annulation progressed through Knoevenagel/Michael/Michael/Michael sequence for the synthesis of b is-spirocyclohexane.

Language: Английский

Cooperative photoactivation/Lewis base catalyzed [4 + 2] annulations of α-diazoketones andortho-amino MBH carbonates to access dihydroquinolinone frameworks DOI
Jin Zhou, Chen Chen, Qiwen Pang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(4), P. 1034 - 1041

Published: Jan. 1, 2023

A series of dihydroquinolinones have been synthesized via synergistic catalysis combining photolysis and Lewis base utilizing in situ generated ketenes ortho -amino MBH carbonates.

Language: Английский

Citations

14
Chemoselective synthesis of α-carboline derivatives via hypervalent iodine-catalyzed [3+3] annulation under metal-free conditions DOI Creative Commons
Shuowen Wang, Rong Li, Shanping Chen

et al.

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: 5(2), P. 112 - 116

Published: Jan. 5, 2023

A strategy for the synthesis of α-carboline derivatives from indole-3-carboxaldehydes and 3-aminocyclohex-2-enones under metal-free conditions has been developed. The combination use phenyliodine (III) diacetate (PIDA) benzoic acid could significantly facilitate corresponding [3 ​+ ​3] annulation process. This newly developed featured unextraordinary chemoselectivity, good functional group tolerance preservation carbonyl ketone substrates, which offers possibility further transformation products.

Language: Английский

Citations

8
A Sc(OTf)3-catalyzed one-pot two-step approach for spiro-oxindole dihydropyridine derivatives initiated by N-olefination of MBH carbonates DOI

Zhen-Hui Yan,

Run Lu,

Cheng Peng

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(9), P. 2294 - 2300

Published: Jan. 1, 2023

An efficient one-pot, two-step, three-component reaction of isatin-derived MBH carbonates, sulfilimines, and epoxides was achieved, thus affording pharmaceutically important spiro-oxindole dihydropyridines.

Language: Английский

Citations

8
Lewis‐Base Dependent (3+3) Annulations of Acetoxy Allenoates with Iminoindolines: α‐Carboline Scaffolds with Varied Substituents DOI

Shubham Debnath,

A. Sanjeeva Kumar,

Sachin Chauhan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(24), P. 4316 - 4332

Published: Nov. 12, 2022

Abstract Lewis base dependent (3+3) annulations of β′ / δ ‐acetoxy allenoates with iminoindolines offer α ‐carbolines varying substituents depending on the used as well subtle changes in reaction conditions. The phosphine‐catalyzed annulation δ‐ acetoxy involves 6‐ exo‐trig cyclization, tosyl anion elimination/trapping, and ethyl acetate elimination key steps delivering β ‐H γ ‐tosyl containing ‐carbolines. An unobvious (by C ‐C bond cleavage) −CH 2 CO Et moiety is observed here. same reactants under DBU catalysis that retain but are devoid −Ts group via 6‐exo‐dig cyclization. β′‐ allenoate completely tertiary amine dependent; use DABCO affords tetrahydro‐ exclusively excellent stereoselectivity while offers substituted distinct from those using DABCO. Several control experiments HRMS studies have been done support a plausible mechanism. magnified image

Language: Английский

Citations

13
Recent advances in the synthetic applications of Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes DOI
Sudheesh T. Sivanandan, Divya K. Nair, Irishi N. N. Namboothiri

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(31), P. 6243 - 6262

Published: Jan. 1, 2023

This article reviews the recent applications of Morita–Baylis–Hillman and Rauhut–Currier adducts nitroalkenes. It also covers mechanistic aspects, including key intermediates reaction pathways.

Language: Английский

Citations

7
One-pot π-extension approach of iminoindoles-to-α-carbolines as blue-light emitters using the cooperative basic system DOI

Rajni Lodhi,

S Banuprakash Goud,

Sampak Samanta

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(32), P. 14163 - 14169

Published: Jan. 1, 2024

Efficient access to α-carbolines was achieved via a domino reaction between iminoindoles and arylidene malononitriles using DABCO/NaHCO 3 as cooperative basic system. The synthesized scaffolds display blue emissions with good quantum yields.

Language: Английский

Citations

2
Organocatalytic Regio- and Enantioselective Allylic Alkylation of Indolin-2-imines with MBH Carbonates toward 3-Allylindoles DOI

Lunfeng Chen,

Pengfei Li

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(12), P. 7810 - 7814

Published: Jan. 26, 2023

An organocatalytic asymmetric C3-allylic alkylation of indolone-2-imines with MBH carbonates has been developed for the first time. As opposed to previous reports, an "interrupted" annulation was achieved, affording 3-allylindoles in generally high yields excellent stereoselectivities. The representative scale-up reaction and transformation were examined. A possible mechanism also proposed.

Language: Английский

Citations

6
Chemoselective three-component synthesis of α-carbolines under metal-free conditions DOI
Wei Feng, Chao Zhang, Xinlin Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(21), P. 5457 - 5462

Published: Jan. 1, 2023

An I 2 O 5 -promoted chemoselective three-component tandem reaction of indole-3-carboxaldehydes, ammonium acetate, and alkynes for the construction α-carbolines under metal-free conditions has been described.

Language: Английский

Citations

5
One‐Pot Regio‐ and Diastereoselective Synthesis of Tetrahydro‐α‐carbolines via Cascade Reactions of Iminoindolines with Morita‐Baylis‐Hillman Bromides of Nitroalkenes DOI
Sudheesh T. Sivanandan, Diksha Chauhan, Irishi N. N. Namboothiri

et al.

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2022(3)

Published: Dec. 24, 2021

Abstract A mild and metal‐free method for the one‐pot synthesis of highly substituted tetrahydro‐ α ‐carbolines from Morita‐Baylis‐Hillman (MBH) bromides nitroalkenes iminoindolines has been demonstrated. Cascade reaction MBH with tosyliminoindolines occurs regio‐ as well diastereoselectivity in a formal [3+3] manner to form various wide substrate scope under conditions. All products were obtained high yields within short time. Also, synthetic efficiency methodology was demonstrated by gram scale experiment further converting them into 3‐nitro‐ ‐carbolines.

Language: Английский

Citations

12
Enantioselective Synthesis of 3‐Allylindoles from Indolin‐2‐imines and MBH Carbonates via Nucleophilic Catalysis DOI

Lunfeng Chen,

Pengfei Li

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(6)

Published: Feb. 7, 2024

Abstract With chiral amine (DHQD) 2 PHAL as nucleophilic catalyst, asymmetric synthesis of enantioenriched 3‐allylindoles was achieved from indolone‐2‐imines and MBH carbonates. Compared with our previous phosphine catalysis, the had exactly opposite effect in terms enantioselectivity. Importantly, we could obtain each enantiomer by adjusting catalyst system.

Language: Английский

Citations

1