Reaction of Ethyl 5-Substituted-2-furoylmalonates with Secondary Amines

Rudolf Kada; Jarmila Bruncková; Pavol Bobál'

doi:10.1135/cccc19941400

Reaction of Ethyl 5-Substituted-2-furoylmalonates with Secondary Amines

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19941400 ◽

1994 ◽

Vol 59 (6) ◽

pp. 1400-1407 ◽

Cited By ~ 1

Author(s):

Rudolf Kada ◽

Jarmila Bruncková ◽

Pavol Bobál'

Keyword(s):

Nucleophilic Substitution ◽

Secondary Amines ◽

Ethyl Malonate ◽

Magnesium Salts

In situ prepared magnesium salts of ethyl malonate react with 5-X-2-furoyl chlorides (X = Br, NO2, C6H5S and C6H5SO2) to give the corresponding ethyl 5-X-2-furoylmalonates. On treatment of these compounds with secondary amines no nucleophilic substitution of the group X in position 5 of the furan nucleus took place but, instead, amides of 5-X-2-furancarboxylic acids were isolated.

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A Novel Nucleophilic Substitution of in Situ Generated 3-tert-Butyldimethyl- silyloxyalk-2-enylsulfonium Salts with Allylindium Reagents

Organic Letters ◽

10.1021/ol016542i ◽

2001 ◽

Vol 3 (20) ◽

pp. 3205-3207 ◽

Cited By ~ 24

Author(s):

Phil Ho Lee ◽

Kooyeon Lee ◽

Sunggak Kim

Keyword(s):

Nucleophilic Substitution

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Aromatic nucleophilic substitution reactions of 1-dialkylamino-2,4-dinitronaphthalene with primary or secondary amines in organic solvents: facile amine–amine exchange

Journal of the Chemical Society Chemical Communications ◽

10.1039/c39880000698 ◽

1988 ◽

pp. 698-700 ◽

Cited By ~ 4

Author(s):

Shizen Sekiguchi ◽

Tohru Horie ◽

Tohru Suzuki

Keyword(s):

Nucleophilic Substitution ◽

Organic Solvents ◽

Secondary Amines ◽

Substitution Reactions ◽

Aromatic Nucleophilic Substitution ◽

Nucleophilic Substitution Reactions ◽

Amine Amine

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In situ nucleophilic substitution reaction ofN,N-dialkylaminoethyl-2-chlorides monitored by gas chromatography/mass spectrometry

Rapid Communications in Mass Spectrometry ◽

10.1002/rcm.2581 ◽

2006 ◽

Vol 20 (14) ◽

pp. 2209-2214 ◽

Cited By ~ 7

Author(s):

V. V. S. Lakshmi ◽

T. Jagadeshwar Reddy ◽

M. R. V. S. Murty ◽

S. Prabhakar ◽

M. Vairamani

Keyword(s):

Mass Spectrometry ◽

Gas Chromatography ◽

Nucleophilic Substitution ◽

Substitution Reaction ◽

Nucleophilic Substitution Reaction ◽

Gas Chromatography Mass Spectrometry ◽

Chromatography Mass Spectrometry

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ChemInform Abstract: Nucleophilic Substitution Reaction of 2,4,6-Tris(trinitromethyl)-1,3,5- triazine. Part 1. Interaction of 2,4,6-Tris(trinitromethyl)-1,3,5- triazine with Alcohols, Diols, Ammonia, and Secondary Amines.

ChemInform ◽

10.1002/chin.199604188 ◽

2010 ◽

Vol 27 (4) ◽

pp. no-no

Author(s):

A. V. SHASTIN ◽

T. I. GODOVIKOVA ◽

S. P. GOLOVA ◽

L. I. KHMEL'NITSKII ◽

B. L. KORSUNSKII

Keyword(s):

Nucleophilic Substitution ◽

Substitution Reaction ◽

Nucleophilic Substitution Reaction ◽

Secondary Amines

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Functional Group Protection

Organic Synthesis ◽

10.1093/oso/9780199965724.003.0014 ◽

2013 ◽

Author(s):

Douglass F. Taber

Keyword(s):

Secondary Amines ◽

Primary Amines ◽

Silyl Ether ◽

Southern Illinois ◽

Convenient Procedure ◽

North Eastern ◽

National University ◽

Facile Preparation ◽

The University

Bekington Myrboh of North-Eastern Hill University reported (Tetrahedron Lett. 2010, 51, 2862) a convenient procedure for the oxidative removal of a 1,3-oxathiolane 1 or a 1,3-dithiolane. Sang-Gyeong Lee and Yong-Jin Yoon of Gyeongsang National University developed (J. Org. Chem. 2010, 75, 484) the pyridazin-3(2H )-one 4 for the microwave-mediated deprotection of an oxime 3. Dario M. Bassani of Université Bordeaux 1 and John S. Snaith of the University of Birmingham devised (J. Org. Chem. 2010, 75, 4648) a procedure for the facile preparation of esters such as 6. Brief photolysis (350 nm) returned the parent carboxylic acid 7. Craig M. Williams of the University of Queensland prepared (Tetrahedron Lett. 2010, 51, 1158) the trithioorthoester 8 by iterative opening of epichlorohydrin. He found that the keto ester 9 could be efficiently released by Hg-mediated hydrolysis. Masatoshi Mihara of the Osaka Municipal Technical Research Institute established (Synlett 2010, 253) that even very congested alcohols such as 10 could be acetylated by acetic anhydride containing a trace of FeCl3. Colleen N. Scott, now at Southern Illinois University, developed (J. Org. Chem. 2010, 75, 253) a convenient procedure for the preparation of the hydridosilane 13, which on Mn catalysis added the alcohol 12 to make the unsymmetrical bisalkoxysilane 14. Sabine Berteina-Raboin of the Université d’Orléans found (Tetrahedron Lett. 2010, 51, 2115) that NaBH4 in EtOH cleanly removed the chloroacetates from 15. Both other esters and silyl ethers were stable under these conditions. Ram S. Mohan of Illinois Wesleyan University established (Tetrahedron Lett. 2010, 51, 1056) that Fe(III) tosylate in methanol selectively removed the alkyl silyl ether from 17 without affecting the aryl silyl ether. Alakananda Hajra and Adinath Majee of Visva-Bharati University effected (Tetrahedron Lett. 2010, 51, 2896) formylation of an amine 19 by heating with commercial 85% formic acid as the solvent in a sealed tube at 80°C. Although both primary and secondary amines could be effi ciently formylated, the primary amines were much more reactive. Doo Ok Jang of Yonsei University found (Tetrahedron Lett. 2010, 51, 683) that the conveniently handled CF3CCO2H (the acid chloride is a gas) could be activated in situ to selectively convert 22 into 24.

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