Journal ArticleDOI
Versatile Synthesis of Functionalized Tetrahydroisoquinolines by Ring Transformation of 2H-Pyran-2-ones
Priyanka B. Kole,Fateh V. Singh +1 more
TLDR
In this article, an efficient synthesis of highly substituted tetrahydroisoquinolines from 2H-pyran-2-ones via nucleophile-mediated ring transformation with tert-butyl-4-oxopiperidine-1-carboxylate followed by acid-mediated cleavage of the tertbutyloxycarbonyl group was demonstrated.Abstract:
Functionalized tetrahydroisoquinolines are convenient precursors for the construction of numerous heterocyclic compounds of therapeutic importance. In this paper we have illustrated an efficient synthesis of highly substituted tetrahydroisoquinolines from 2H-pyran-2-ones via nucleophile-mediated ring transformation with tert-butyl-4-oxopiperidine-1-carboxylate followed by acid-mediated cleavage of the tert-butyloxycarbonyl group. The products were achieved smoothly in high yields with flexibility of various substituents.read more
Citations
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Journal ArticleDOI
Base-mediated alternate route for multi-functionalized allylbenzenes using ring transformation strategy
TL;DR: A simple yet innovative approach for the construction of multi-substituted allylbenzenes 14, 16 and 18 with "donor-acceptor" functionalities has been delineated through base-mediated ring transform.
Journal ArticleDOI
Metal-free synthesis and characterization of 1,3-Bis(heteroaryl)benzenes followed by the photophysical studies using ultraviolet–visible and fluorescence spectroscopy
R. Kanimozhi,Fateh V. Singh +1 more
TL;DR: In this article, a carbanion-induced ring transformation reaction of 6-heteroaryl-2H-pyran-2-ones 4 and 7 with heteroarylketones 5 and 8 was described.
Journal ArticleDOI
Metal-Free Synthesis of Thermally Stable Fluorescent p-Terphenyls by Ring Transformation of 2H-Pyran-2-ones
Journal ArticleDOI
Synthesis, spectral characterization and photophysical studies of tetrahydroquinolines
TL;DR: In this paper, a metal-free, ultrasound-assisted, fast synthesis of fluorescent N-Boc-protected 1,2,3,4-tetrahydroquinolines 9a-p was described through carbanion-induced ring transformation of 6-aryl-2H-pyran-2-ones with tert-butyl 3-oxopiperidine-1-carboxylate under basic condition.
Journal ArticleDOI
Investigation of Pharmaceutical Importance of 2H-Pyran-2-One Analogues via Computational Approaches
Samata E. Shetgaonkar,Shiva Prasad Kollur,Renjith Raveendran Pillai,Karthick Thangavel,Sanja J. Armaković,Stevan Armaković,Chandan Shivamallu,Raghavendra G. Amachawadi,Asad Syed,Abdallah M. Elgorban,Ali H. Bahkali,Fateh V. Singh +11 more
TL;DR: In this paper, high functionalized spirocyclic ketals were synthesized through asymmetric oxidative spirocycle via carbanion-induced ring transformation of 2H-pyran-2-ones with 1,4-cyclohexandione monoethyleneketal under alkaline conditions.
References
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Journal ArticleDOI
Natural and synthetic 2H-pyran-2-ones and their versatility in organic synthesis☆
Atul Goel,Vishnu Ji Ram +1 more
TL;DR: An overview of the natural presence and development of the chemistry of the 2 H -pyran-2-one ring system is delineated in this article, where 363 references are provided.
Journal ArticleDOI
Strong Brønsted acid promoted asymmetric hydrogenation of isoquinolines and quinolines catalyzed by a Rh–thiourea chiral phosphine complex via anion binding
TL;DR: Catalyzed by a Rh/bisphosphine–thiourea (L1) complex, isoquinolines and quinolines are hydrogenated with high conversions and high enantioselectivities.
Journal ArticleDOI
Enantioselective iridium-catalyzed hydrogenation of 3,4-disubstituted isoquinolines.
TL;DR: A highly efficient direct enantioselective iridium-catalyzed hydrogenation of 3,4-disubstituted isoquinolines is described, demonstrating that iodine can significantly improve the performance of an iridium catalyst in asymmetric hydrogenation.
Journal ArticleDOI
Synthesis and reaction of 6‐substituted 3‐methoxycarbonyl‐4‐methylthio‐2H‐pyran‐2‐one derivatives
Journal ArticleDOI
A one-pot bicycloannulation method for the synthesis of tetrahydroisoquinoline systems.
TL;DR: A highly effective method for the synthesis of the core indolo[2,3-alpha]quinolizidine skeleton found in yohimbine is described, which results in several tetrahydroisoquinoline alkaloids in good yield.
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