scholarly journals Synthesis of New 5-Aryl-benzo[f][1,7]naphthyridines via a Cascade Process (Ugi-3CR/Intramolecular Aza-Diels-Alder Cycloaddition)/Aromatization

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 2029
Author(s):  
Óscar Vázquez-Vera ◽  
Daniel Segura-Olvera ◽  
Mónica Rincón-Guevara ◽  
Atilano Gutiérrez-Carrillo ◽  
Miguel García-Sánchez ◽  
...  
Keyword(s):  
Oxidation Process ◽  
Diels Alder ◽  
Cascade Process ◽  
Chain Ring ◽  
One Pot ◽  
The Core ◽  
Sar Studies ◽  
Starting Point ◽  
Three Component Reaction

A series of eight new 5-aryl-benzo[f][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi–three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[f][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[f][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before.

scholarly journals (E)-2-(2-oxo-4-phenylbut-3-en-1-yl)benzo[d]thiazole-3(2H)-carboxylates

Molbank ◽  
10.3390/m1236 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1236
Author(s):  
Yordan Stremski ◽  
Stela Statkova-Abeghe
Keyword(s):  
13C Nmr ◽  
One Pot ◽  
Three Component Reaction

An convenient one-pot approach for the synthesis of new (E)-2-(2-oxo-4-phenylbut-3-en-1-yl)benzo[d]thiazole-3(2H)-carboxylates is demonstrated. The method is based on a three-component reaction of benzylideneacetone with electrophilic N-alkoxycarbonylbenzothiazolium species formed in situ. The newly synthesized compounds were fully characterized by 1D 1H, 13C- NMR, IR and MS.

One-Pot Synthesis of ABC Type Triblock Copolymers via in situ Click [3 + 2] and Diels−Alder [4 + 2] Reactions

2007 ◽  
Vol 40 (2) ◽  
pp. 191-198 ◽  
Author(s):  
Hakan Durmaz ◽  
Aydan Dag ◽  
Ozcan Altintas ◽  
Tuba Erdogan ◽  
Gurkan Hizal ◽  
...  
Keyword(s):  
Triblock Copolymers ◽  
Diels Alder ◽  
One Pot ◽  
One Pot Synthesis

Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds

2019 ◽  
Author(s):  
Evan Darzi ◽  
Joyann Barber ◽  
Neil Garg
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Polycyclic Aromatic Hydrocarbon ◽  
Aromatic Hydrocarbon ◽  
Aromatic Hydrocarbons ◽  
Diels Alder ◽  
Pericyclic Reactions ◽  
One Pot ◽  
Synthetic Strategy ◽  
Polycyclic Aromatic

We report a modular synthetic strategy for accessing heteroatom-containing polycyclic aromatic hydrocarbons (PAHs) that relies on the controlled generation of transient heterocyclic alkynes and arynes. The strained intermediates undergo in situ trapping with readily accessible oxadiazinones. Four sequential pericyclic reactions occur, namely two Diels–Alder / retro-Diels–Alder sequences, which can be performed in a stepwise or one-pot fashion to assemble four new carbon–carbon (C–C) bonds.

scholarly journals Synthesis of oxa-bridged derivatives from Diels–Alder bis-adducts of butadiene and 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene

2010 ◽  
Vol 6 ◽  
Author(s):  
Faiz Ahmed Khan ◽  
Karuppasamy Parasuraman
Keyword(s):  
Diels Alder ◽  
One Pot ◽  
Excellent Yield ◽  
Catalyzed Oxidation

Bis-adducts of 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene and 1,3-butadiene, generated in situ from 3-sulfolene, have been synthesized in excellent yield. Ruthenium catalyzed oxidation of the bis-adducts followed by a one-pot transformation of the resulting α-diketone furnished oxa-bridged compounds. Unambiguous stereochemical assignments of both diastereomeric series are reported.

1996 Merck Frosst Award Lecture Synthetic adventures along a Rocky Mountain road

1997 ◽  
Vol 75 (9) ◽  
pp. 1163-1171 ◽  
Author(s):  
Brian A. Keay ◽  
Shawn P. Maddaford ◽  
Walter A. Cristofoli ◽  
Neil G. Andersen ◽  
Marco S. Passafaro ◽  
...  
Keyword(s):  
Suzuki Reaction ◽  
Rocky Mountain ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Aldehydes And Ketones ◽  
Palladium Catalyzed ◽  
Therapeutic Research

This paper describes the chemistry presented during the Merck Frosst Centre for Therapeutic Research Lecture Award given at the 79th Chemistry in Canada Conference held in St. John's, Newfoundland in June 1996. The first section describes the synthesis of (+)-xestoquinone using an asymmetric palladium-catalyzed polyene cyclization as the key step that creates the C and D rings and the stereogenic centre (68% ee) in one step. Extensions of the work involving an in situ Suzuki reaction are presented. The synthesis of C2-symmetric biaryls and the synthesis of a recently isolated binaphthyl natural product is described using this new method. A new one-pot desilylation–oxidation procedure of silyl ethers is described in detail for the preparation of aldehydes and ketones directly without the need for the isolation of the alcohol intermediate. Finally, a highly diastereoselective (>97%) Diels–Alder reaction is presented using (+)-cis,cis-spiro[4.4]nonane-1,6-diol as a new chiral auxiliary. One of the alcohols is attached to a pivalate, the other to an acrylate, and the Diels–Alder reaction with cyclopentadiene provides only one adduct (by 1H NMR and HPLC) with the endo stereochemistry. Keywords: (+)-xestoquinone, asymmetric palladium-catalyzed polyene cyclization, in situ Suzuki reaction, desilylation–oxidation reaction, spirodiols, chiral auxiliaries.

Insight into growth of Au–Pt bimetallic nanoparticles: anin situXAS study

2017 ◽  
Vol 24 (4) ◽  
pp. 825-835 ◽  
Author(s):  
Chandrani Nayak ◽  
D. Bhattacharyya ◽  
K. Bhattacharyya ◽  
A. K. Tripathi ◽  
R. D. Bapat ◽  
...  
Keyword(s):  
Bimetallic Nanoparticles ◽  
Energy Dispersive ◽  
Core Shell ◽  
One Pot ◽  
X Ray ◽  
The Core ◽  
One Pot Synthesis ◽  
X Ray Absorption ◽  
Insight Into

Au–Pt bimetallic nanoparticles have been synthesized through a one-pot synthesis route from their respective chloride precursors using block copolymer as a stabilizer. Growth of the nanoparticles has been studied by simultaneousin situmeasurement of X-ray absorption spectroscopy (XAS) and UV–Vis spectroscopy at the energy-dispersive EXAFS beamline (BL-08) at Indus-2 SRS at RRCAT, Indore, India.In situXAS spectra, comprising both X-ray near-edge structure (XANES) and extended X-ray absorption fine-structure (EXAFS) parts, have been measured simultaneously at the Au and PtL3-edges. While the XANES spectra of the precursors provide real-time information on the reduction process, the EXAFS spectra reveal the structure of the clusters formed in the intermediate stages of growth. This insight into the formation process throws light on how the difference in the reduction potential of the two precursors could be used to obtain the core–shell-type configuration of a bimetallic alloy in a one-pot synthesis method. The core–shell-type structure of the nanoparticles has also been confirmed byex situenergy-dispersive spectroscopy line-scan and X-ray photoelectron spectroscopy measurements within situion etching on fully formed nanoparticles.

Sign in / Sign up

Export Citation Format

Share Document