Computational study on the synthesis of 1-phenyl-3,4-dihydro-β-carboline: T3P®-promoted one-pot formation from tryptamine vs. POCl3-mediated ring closure of Nb-benzoyltryptamine. The first DFT investigation of the Bischler-Napieralski reaction

2016 ◽  
Vol 1097 ◽  
pp. 48-60 ◽  
Author(s):  
Péter Ábrányi-Balogh ◽  
Balázs Volk ◽  
György Keglevich ◽  
Mátyás Milen
Keyword(s):  
Computational Study ◽  
Ring Closure ◽  
One Pot

Catalyst-Free One-Pot Synthesis of Novel Heteroarylamine Substituted Furo[3,2-c]coumarins

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1589-1592 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Mahnaz Saraei ◽  
Reyhaneh Khoeiniha
Keyword(s):  
Michael Addition ◽  
Aldol Condensation ◽  
Ring Closure ◽  
Dehydration Reaction ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Tandem Process ◽  
First Time

A high-yielding cyclocondensation of 4-hydroxycoumarin, phenylglyoxal monohydrate, and heteroarylamines proceeds without catalysis, which gives novel functionalized furo[3,2-c]coumarins and heteroarylamino alkylation of coumarin products in acetonitrile under reflux, is reported for the first time. This tandem process involves sequentially an aldol condensation, Michael addition, a ring closure, and dehydration reaction.

scholarly journals A computational study of the influence of methyl substituents on competitive ring closure to α- and β-lactones

2017 ◽  
Vol 15 (34) ◽  
pp. 7235-7240 ◽  
Author(s):  
Philippe B. Wilson ◽  
Ian H. Williams
Keyword(s):  
Computational Study ◽  
Ring Closure

gem-Dimethyl substitution at C3 enhances the preference for β-lactone formation from 2-chlorosuccinate but methylation at C2 almost favours α-lactone.

The Structure and Synthesis of Cytokinin Metabolites. 1. The 7- and 9-β-D-Glucofuranosides and Pyranosides of Zeatin and 6-Benzylaminopurine

1978 ◽  
Vol 31 (5) ◽  
pp. 1095 ◽  
Author(s):  
DE Cowley ◽  
CC Duke ◽  
AJ Liepa ◽  
JK Macleod ◽  
DS Letham
Keyword(s):  
Pyrimidine Ring ◽  
Ring Closure ◽  
Imidazole Derivative ◽  
High Yield ◽  
Ring Size ◽  
Plant Metabolites ◽  
One Pot ◽  
Synthetic Routes

The structures of the major stable plant metabolites of the cytokinins zeatin and 6-benzylaminopurine have been confirmed by synthesis to be 7- and 9-β-D-glucopyranosides. The small quantities of metabolites initially isolated (< 100 μg) precluded assignment of the glucose ring size or configuration of the anomeric linkage so that synthesis of both the furanose and pyranose forms of 7-β-D- and 9-β-D-glucosylzeatin and 6-benzylaminopurine was undertaken which allowed direct u.v., m.s. and t.l.c. comparison with the metabolites. Numerous synthetic routes to the unusual 7-glucosides of the two cytokinins were explored, the most successful utilizing a one-pot pyrimidine ring closure of an imidazole derivative to afford directly in high yield the required 7-glucosides of zeatin and 6-benzylaminopurine.

scholarly journals A rare γ-pyranopyrazole skeleton: design, one-pot synthesis and computational study

2016 ◽  
Vol 14 (31) ◽  
pp. 7490-7494 ◽  
Author(s):  
Muhammed Üçüncü ◽  
Ceren Cantürk ◽  
Erman Karakuş ◽  
Hüseyin Zeybek ◽  
Uğur Bozkaya ◽  
...  
Keyword(s):  
Computational Study ◽  
Synthetic Method ◽  
One Pot ◽  
One Pot Synthesis

A base mediated one-pot, two-step synthetic method for constructing γ-pyranopyrazoles.

Synthesis of novel N-functionalized 4-aryl-tetrahydrobiquinoline-2,5-(1H,3H)-diones via one-pot three-component reaction: a joint experimental and computational study

2018 ◽  
Vol 96 (12) ◽  
pp. 1071-1078
Author(s):  
Vahideh Zadsirjan ◽  
Sayyed Jalil Mahdizadeh ◽  
Majid M. Heravi ◽  
Masumeh Heydari
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Computational Study ◽  
Reaction Pathway ◽  
Deep Insight ◽  
One Pot ◽  
Functional Theory ◽  
Three Component Reaction ◽  
High Yields ◽  
Mechanism Of The Reaction

A novel series of N-functionalized 4-aryl-tetrahydrobiquinoline-2,5-(1H,3H)-diones were synthesized in high yields by a one-pot three-component reaction involving 2-chloroquinoline-3-carbaldehydes, Meldrum’s acid, and enaminones (dimedone-based enaminones) in the presence of K2CO3 in CH3CN under reflux condition. To gain a deep insight on the mechanism of the reaction, an extensive series of quantum mechanics calculations in the framework of density functional theory (DFT) were carried out for supporting the suggested reaction pathway.

scholarly journals One-Pot Synthesis of Novel Dibenzoxanthenes, Diarylbutanes, and Calix[4]resorcinarenes via Consecutive Pyrrolidine Ring-Closure/Ring-Opening Reactions

2019 ◽  
Vol 2019 ◽  
pp. 1-7
Author(s):  
Andrey V. Smolobochkin ◽  
Almir S. Gazizov ◽  
Alexander R. Burilov ◽  
Michail A. Pudovik
Keyword(s):  
Ring Opening ◽  
Ring Closure ◽  
Acidic Media ◽  
Pyrrolidine Ring ◽  
One Pot ◽  
One Pot Synthesis ◽  
Ring Opening Reactions

Herein, we report the approach to the otherwise hardly accessible dibenzoxanthenes, diarylbutanes, and calix[4]resorcinarenes possessing urea moieties based on the reaction of N-(4,4-diethoxybutyl)ureas with electron-rich aromatics in strongly acidic media. Unlike the previously developed methods, the proposed approach benefits from one-pot procedure and allows to obtain the target compounds with much higher yields.

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