scholarly journals Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure

2021 ◽  
Vol 17 ◽  
pp. 2511-2519
Author(s):  
Agnieszka Grajewska ◽  
Maria Chrzanowska ◽  
Wiktoria Adamska
Keyword(s):  
Carboxylic Acids ◽  
Core Structure ◽  
Cyclization Reaction ◽  
Chemical Behavior ◽  
Petasis Reaction ◽  
Simple Protocol ◽  
Hcl Solution

A convenient and simple protocol has been developed for the synthesis of a series of new tetracyclic tetrahydroisoquinoline derivatives, 7,12-dihydro-6,12-methanodibenzo[c,f]-azocine-5-carboxylic acids by three component Petasis reaction with the use of aminoacetaldehyde acetals bearing substituted benzyl groups as the amine components followed by Pomeranz–Fritsch double cyclization reaction. By applying this method, several acids have been prepared in satisfactory yields. An unprecedented chemical behavior of a Petasis reaction product in diluted HCl solution leading to the formation of a phenylglycine derivative has been observed and the mechanism explaining such reactivity has been proposed.

scholarly journals Synthesis of Indoloquinolines: An Intramolecular Cyclization Leading to Advanced Perophoramidine-Relevant Intermediates

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 6039
Author(s):  
Craig A. Johnston ◽  
David B. Cordes ◽  
Tomas Lebl ◽  
Alexandra M. Z. Slawin ◽  
Nicholas J. Westwood
Keyword(s):  
Natural Product ◽  
Intramolecular Cyclization ◽  
Crystallographic Analysis ◽  
Core Structure ◽  
Cyclization Reaction ◽  
Alternative Route ◽  
X Ray ◽  
The Core ◽  
Bioactive Natural Product ◽  
Synthetic Target

The bioactive natural product perophoramidine has proved a challenging synthetic target. An alternative route to its indolo[2,3-b]quinolone core structure involving a N-chlorosuccinimde-mediated intramolecular cyclization reaction is reported. Attempts to progress towards the natural product are also discussed with an unexpected deep-seated rearrangement of the core structure occurring during an attempted iodoetherification reaction. X-ray crystallographic analysis provides important analytical confirmation of assigned structures.

scholarly journals Metal-free selective mono-halodecarboxylation of heteroarenes under mild conditions

2018 ◽  
Vol 5 (6) ◽  
pp. 180333 ◽  
Author(s):  
Scott H. Henderson ◽  
Ryan A. West ◽  
Simon E. Ward ◽  
Mark A. Honey
Keyword(s):  
Carboxylic Acids ◽  
Toxic Metal ◽  
Metal Catalysts ◽  
Metal Free ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Convenient Route

The halodecarboxylation of heteroarene carboxylic acids by treatment with N -bromosuccinimide or N -chlorosuccinimide was performed. This procedure provides a convenient route to synthetically useful mono-halogenated heteroarene intermediates such as halo-indoles, -aza-indoles, -indazoles and -aza-indazoles. The mild conditions employed and simple protocol provides an advantage over traditional halodecarboxylation procedures that require expensive and toxic metal catalysts, basic conditions, time-consuming intermediate isolation and elevated reaction temperatures.

ChemInform Abstract: A Concise Synthesis of Tetrahydroisoquinoline-1-carboxylic Acids Using a Petasis Reaction and Pomeranz-Fritsch-Bobbitt Cyclization Sequence.

ChemInform ◽  
2012 ◽  
Vol 43 (35) ◽  
pp. no-no
Author(s):  
Maria Chrzanowska ◽  
Agnieszka Grajewska ◽  
Zofia Meissner ◽  
Maria Rozwadowska ◽  
Iwona Wiatrowska
Keyword(s):  
Carboxylic Acids ◽  
Petasis Reaction

ChemInform Abstract: A Simple Protocol for Cu-Catalyzed Protodecarboxylation of (Hetero)aromatic Carboxylic Acids.

ChemInform ◽  
2016 ◽  
Vol 47 (35) ◽  
Author(s):  
Zhaojie Li ◽  
Zhengjiang Fu ◽  
Haixia Zhang ◽  
Jiao Long ◽  
Yuanyuan Song ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Aromatic Carboxylic Acids ◽  
Simple Protocol

Synthesis of carbonylated heteroaromatic compounds via visible-light-driven intramolecular decarboxylative cyclization of o-alkynylated carboxylic acids

2017 ◽  
Vol 53 (61) ◽  
pp. 8533-8536 ◽  
Author(s):  
Fei Gao ◽  
Jiu-Tao Wang ◽  
Lin-Lin Liu ◽  
Na Ma ◽  
Chao Yang ◽  
...  
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Cyclization Reaction ◽  
Easy Access ◽  
Heteroaromatic Compounds ◽  
Efficient Strategy ◽  
Visible Light Driven ◽  
Decarboxylative Cyclization

An efficient strategy for the easy access to carbonylated heteroaromatic compounds has been developed via a visible-light-promoted intramolecular decarboxylative cyclization reaction of o-alkynylated carboxylic acids.

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