C–H Functionalization of Imidazo[1,5-a]pyridines: A Metal-Free Approach for Methylene Insertion to Access C(sp2)–C(sp3)–H–C(sp2) Bond Formation DOI Creative Commons

Shivangani Mahajan,

Sanghapal D. Sawant

ACS Omega, Journal Year: 2024, Volume and Issue: 9(50), P. 49071 - 49080

Published: Dec. 5, 2024

Formaldehyde has been used as a solvent and source of carbon to insert methylene group for bridging two imidazo[1,5-

Language: Английский

Unlocking Diversity: From Simple to Cutting-Edge Synthetic Methodologies of Bis(indolyl)methanes DOI
Pankaj Teli, Shivani Soni, Sunita Teli

et al.

Topics in Current Chemistry, Journal Year: 2024, Volume and Issue: 382(1)

Published: Feb. 25, 2024

Language: Английский

Citations

13
Indolyl‐Ynones: Building Blocks for Molecular Diversity DOI
Ahalya Behera

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1044 - 1058

Published: Jan. 12, 2024

Abstract This review centers on the synthetic strategies employed with indolyl‐ynones. Indolyl‐ynone, owing to its highly reactive ynone moiety, frequently partakes in dearomatizing spirocyclization reactions and subsequent rearrangement when subjected various reaction conditions. Hence, heterocycles such as densely functionalized spiroindolenines, carbazoles, quinolines carbo‐and hetero‐cycle substituted indoles are synthesized from In addition this, versatile spirocyclic indole scaffold exhibits capability produce tetracyclic polyclic structures through intricate skeletal processes. Moreover, total synthesis of natural products using indolyl‐ynone moiety was also compiled this review.

Language: Английский

Citations

5
Short Total Synthesis of (+)-Colletotryptins B-D and Mucronatin B Derivative DOI Creative Commons

Wilailak Saetae,

Chayamon Chantana,

Saowanit Saithong

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8620 - 8631

Published: May 29, 2024

The short and first total synthesis of (+)-colletotryptins B-D, ent-colletotryptin A, diastereomer mucronatin B, which are a group natural 3-(indol-2-yl)-3-(indol-3-yl)-1,2-propanediol (IIPDO) analogues containing two stereogenic centers at the C8′ C9′ positions, isolated from endophytic fungus Colletotrichum sp. SC1355 Tetrapterys mucronata, respectively, has been successfully accomplished in three steps with overall yields ranging 28 to 54%. Key features this include an innovative Bi(OTf)3-catalyzed stereoselective transindolylation (S)-3,3′-di(1H-indol-3-yl)propane-1,2-diol. operational simplicity, environmentally friendly catalyst, broad functional tolerance modular strategy render it suitable for adoption both academic industrial settings.

Language: Английский

Citations

5
Visible light-assisted H4[PW11VO40] catalysed synthesis of bis(indolyl)methanes DOI

Gopika Jagannivasan,

Gopika N Nair,

Suja Haridas

et al.

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 547, P. 113285 - 113285

Published: June 10, 2023

Language: Английский

Citations

11
Iodocycloisomerization/Nucleophile Addition Cascade Transformations of 1,2-Alkynediones DOI
Debojyoti Bag, Harpreet Kour,

Nirjhar Saha

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 2377 - 2384

Published: Feb. 2, 2023

A general electrophilic iodocyclization/nucleophile addition cascade transformation for 1,2-alkynediones the synthesis of various oxygen heterocycles and access to regioselective alkyne hydroxylation is reported. Furan-tethered ynediones resulted in construction exo-enol ethers via carbonyl-alkyne cyclization-initiated heteroarene dearomatization, whereas other (hetero)arene-, alkenyl-, alkyl-tethered formation highly functionalized 3(2H)-furanones. Importantly, developed domino protocols involve important heterocyclic scaffolds installation two functional groups a single operation. Moreover, use water as nucleophile furanone ring opening. The are characterized by wide substrate scope, their utility has been demonstrated number postsynthetic transformations.

Language: Английский

Citations

10
Divergent Synthesis of Unsymmetrical Bis-heteroaryl Ketones via Base-Promoted Cascade Reactions of 1,2-Alkynedione-Derived N-Propargylic β-Enaminones DOI
Debojyoti Bag,

Sheetal Saini,

Mahesh S. Rathod

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11665 - 11670

Published: Aug. 6, 2024

Herein we disclose a transition-metal-free, one-pot two-step strategy for the synthesis of unsymmetrical bis-heteroaryl ketones.

Language: Английский

Citations

3
Ag(i)-catalyzed dearomatizing spirocyclization/nucleophile addition cascade reactions of indole-tethered ynones DOI
Debojyoti Bag, Sanghapal D. Sawant

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(84), P. 12649 - 12652

Published: Jan. 1, 2023

Ag( i )-catalyzed highly diastereoselective construction of divergent spiroindolines via dearomatizing indole-ynone spirocyclization/nucleophile addition cascade reaction is disclosed herein.

Language: Английский

Citations

6
Divergent Synthesis of 3-Pyrrolidin-2-yl-1H-indoles, Symmetric and Unsymmetric Bis(Indolyl)Methanes (BIMs) through Photocatalyzed Decarboxylative Coupling/Friedel–Crafts Alkylation Reaction DOI
Patamawadee Silalai, Rungnapha Saeeng

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4052 - 4065

Published: March 7, 2023

This paper reports the acid-controlled divergent synthesis of 3-pyrrolidin-2-yl-1H-indoles and symmetric unsymmetrical bis(indolyl)methanes (BIMs) through photocatalyzed decarboxylative coupling Friedel-Crafts alkylation reactions, respectively. The protocol involves C-H functionalization, switching formation two products, room-temperature conditions, low photocatalyst loadings, without strong oxidant, moderate to excellent yields. method has been applied for natural product vibrindole A 1,1-bis(1H-indol-3-yl)-2-phenylethane.

Language: Английский

Citations

5
Hydrogen-Bonding Activation of Gold(I) Chloride Complexes: Enantioselective Synthesis of 3(2H)-Furanones by a Cycloisomerization-Addition Cascade DOI Creative Commons
Pilar Elías‐Rodríguez, Manuel de La Mata Benítez, Javier Iglesias‐Sigüenza

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 5995 - 6000

Published: July 11, 2024

Enantioselective synthesis of 3(2H)-furanones has been achieved using the intermolecular H-bonding activation gold(I) chloride complexes. A DM-BINAP [(R)-(+)-2,2′-Bis[di(3,5-xylyl)phoshino]-1,1′-binaphthyl] digold(I) dichloride complex in combination with a sulfonyl squaramide (SO2Sq) identified as optimal catalytic system. The process involves 5-endo-dig oxa-cyclization followed by stereocontrolled addition indoles. Interestingly, soft L*Au–Cl allowed recovery both and activator after chromatographic purification.

Language: Английский

Citations

1
Gold catalysis in organic synthesis: fifteen years of research in India DOI
Debasish Mandal, Anil Kumar, Nitin T. Patil

et al.

DELETED, Journal Year: 2022, Volume and Issue: 88(4), P. 501 - 527

Published: Sept. 5, 2022

Gold catalysis has emerged as an important tool in the field of synthetic organic chemistry for selective functionalization C–C multiple bonds. The research India on gold focuses diverse fields starting from methodology developments to synthesis molecular scaffolds their potential application medicinal and material science. Herein, we present a comprehensive overview gold-catalyzed transformations that were reported last fifteen years.

Language: Английский

Citations

3