Literature DB >> 18642832

A versatile cyclodehydration reaction for the synthesis of isoquinoline and beta-carboline derivatives.

Mohammad Movassaghi1, Matthew D Hill.   

Abstract

The direct conversion of various amides to isoquinoline and beta-carboline derivatives via mild electrophilic amide activation, with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine, is described. Low-temperature amide activation followed by cyclodehydration upon warming provides the desired products with short overall reaction times. The successful use of nonactivated and halogenated phenethylene derived amides, N-vinyl amides, and optically active substrates is noteworthy.

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Year:  2008        PMID： 18642832      PMCID： PMC2692836          DOI： 10.1021/ol801264u

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

Review 1.  Asymmetric synthesis of isoquinoline alkaloids.

Authors:  Maria Chrzanowska; Maria D Rozwadowska
Journal:  Chem Rev       Date:  2004-07       Impact factor: 60.622

Review 2.  beta-Phenylethylamines and the isoquinoline alkaloids.

Authors:  Kenneth W Bentley
Journal:  Nat Prod Rep       Date:  2006-05-08       Impact factor: 13.423

3.  Direct synthesis of pyridine derivatives.

Authors:  Mohammad Movassaghi; Matthew D Hill; Omar K Ahmad
Journal:  J Am Chem Soc       Date:  2007-07-31       Impact factor: 15.419

Review 4.  Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions.

Authors:  Juan R Dehli; Julien Legros; Carsten Bolm
Journal:  Chem Commun (Camb)       Date:  2005-01-17       Impact factor: 6.222

5.  Synthesis of pseudo-geminal-, pseudo-ortho-, and ortho-phosphinyl-oxazolinyl-[2.2]paracyclophanes for use as ligands in asymmetric catalysis.

Authors:  Daniel K Whelligan; Carsten Bolm
Journal:  J Org Chem       Date:  2006-06-09       Impact factor: 4.354

6.  Synthetic strategies to a telomere-targeted pentacyclic heteroaromatic salt.

Authors:  Ian Hutchinson; Malcolm F G Stevens
Journal:  Org Biomol Chem       Date:  2006-11-23       Impact factor: 3.876

7.  Single-step synthesis of pyrimidine derivatives.

Authors:  Mohammad Movassaghi; Matthew D Hill
Journal:  J Am Chem Soc       Date:  2006-11-08       Impact factor: 15.419

8.  Palladium-catalyzed anilide ortho-arylation and subsequent one-pot cyclization to phenanthridines.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Org Chem       Date:  2007-09-07       Impact factor: 4.354

9.  Copper-catalyzed coupling of amides and carbamates with vinyl halides.

Authors:  Lei Jiang; Gabriel E Job; Artis Klapars; Stephen L Buchwald
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

10.  Antibacterial and antifungal activity of liriodenine and related oxoaporphine alkaloids.

Authors:  C D Hufford; A S Sharma; B O Oguntimein
Journal:  J Pharm Sci       Date:  1980-10       Impact factor: 3.534
  10 in total
  20 in total

1.  Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin.

Authors:  Huijun Dong; Regina T Latka; Tom G Driver
Journal:  Org Lett       Date:  2011-04-25       Impact factor: 6.005

2.  Rh(II)2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides.

Authors:  Ashley L Pumphrey; Huijun Dong; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

3.  A versatile synthesis of substituted isoquinolines.

Authors:  Chong Si; Andrew G Myers
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-09       Impact factor: 15.336

4.  Delayed catalyst function enables direct enantioselective conversion of nitriles to NH2-amines.

Authors:  Shaochen Zhang; Juan Del Pozo; Filippo Romiti; Yucheng Mu; Sebastian Torker; Amir H Hoveyda
Journal:  Science       Date:  2019-04-05       Impact factor: 47.728

5.  Tandem Cycloisomerization/Suzuki Coupling of Arylethynyl MIDA Boronates.

Authors:  Julian M W Chan; Giovanni W Amarante; F Dean Toste
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

6.  Electrophilic Carbonyl Activation: Competing Condensative Cyclizations of Tryptamine Derivatives.

Authors:  Fan Liu; Mohammad Movassaghi
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

7.  Synthesis of spirocyclic indolines by interruption of the Bischler-Napieralski reaction.

Authors:  Jonathan William Medley; Mohammad Movassaghi
Journal:  Org Lett       Date:  2013-07-05       Impact factor: 6.005

8.  A concise and versatile double-cyclization strategy for the highly stereoselective synthesis and arylative dimerization of Aspidosperma alkaloids.

Authors:  Jonathan William Medley; Mohammad Movassaghi
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-12       Impact factor: 15.336

9.  Direct Observation of Intermediates Involved in the Interruption of the Bischler-Napieralski Reaction.

Authors:  Kolby L White; Marius Mewald; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2015-07-22       Impact factor: 4.354

10.  Synthesis of structurally simplified analogues of pancratistatin: truncation of the cyclitol ring.

Authors:  Madhuri Manpadi; Artem S Kireev; Igor V Magedov; Jeff Altig; Paul Tongwa; Mikhail Yu Antipin; Antonio Evidente; Willem A L van Otterlo; Alexander Kornienko
Journal:  J Org Chem       Date:  2009-09-18       Impact factor: 4.354
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