Yb(OTf)3-Mediated Access to Furans from β-Ketothioamides via Eschenmoser Sulfide Contraction Reaction

2015 ◽  
Vol 80 (24) ◽  
pp. 11999-12005 ◽  
Author(s):  
Ming Li ◽  
Xiang-Jing Kong ◽  
Li-Rong Wen
Keyword(s):  
Sulfide Contraction

A new synthetic method of 1β-methylcarbapenems utilizing the eschenmoser sulfide contraction

1994 ◽  
Vol 35 (14) ◽  
pp. 2187-2190 ◽  
Author(s):  
Osamu Sakurai ◽  
Tsuyoshi Ogiku ◽  
Masami Takahashi ◽  
Hiroshi Horikawa ◽  
Tameo Iwasaki
Keyword(s):  
Synthetic Method ◽  
Sulfide Contraction

A new efficient synthesis of α-methyl-β-ketoesters through an Eschenmoser sulfide reaction

2004 ◽  
Vol 82 (8) ◽  
pp. 1289-1293 ◽  
Author(s):  
Christian Bellec ◽  
Olivier Gaurat
Keyword(s):  
Efficient Synthesis ◽  
Sulfide Contraction

Various α-methyl-β-ketoesters were readily synthesized through Eschenmoser condensation of thioamides with a commercially available bromoester. β-Enaminoesters were easily prepared through this sulfide contraction reaction and were hydrolysed to afford the corresponding β-ketoesters in moderate to good yields.Key words: α-alkylated-β-ketoesters, Eschenmoser, β-enaminoesters.

A Variation of the Sulfide Contraction Procedure for Synthesis of Corrinoid Systems

1973 ◽  
Vol 12 (11) ◽  
pp. 910-912 ◽  
Author(s):  
Erwin Götschi ◽  
Walter Hunkeler ◽  
Hans-Jakob Wild ◽  
Peter Schneider ◽  
Walter Fuhrer ◽  
...  
Keyword(s):  
Contraction Procedure ◽  
Sulfide Contraction

Influence of ring size on the outcome of sulfide contraction reactions with thiolactams. Isolation of bicyclic ketene S,N-acetals and thioisomünchnones

2001 ◽  
pp. 2055-2062 ◽  
Author(s):  
Joseph P. Michael ◽  
Charles B. de Koning ◽  
Christiaan W. van der Westhuyzen ◽  
Manuel A. Fernandes
Keyword(s):  
Ring Size ◽  
Sulfide Contraction

scholarly journals Silica gel and microwave-promoted synthesis of dihydropyrrolizines and tetrahydroindolizines from enaminones

2021 ◽  
Vol 17 ◽  
pp. 2543-2552
Author(s):  
Robin Klintworth ◽  
Garreth L Morgans ◽  
Stefania M Scalzullo ◽  
Charles B de Koning ◽  
Willem A L van Otterlo ◽  
...  
Keyword(s):  
Microwave Heating ◽  
Carbonyl Group ◽  
Silica Gel ◽  
Microwave Power ◽  
Pyrrole Ring ◽  
Microwave Assisted ◽  
Nonpolar Solvents ◽  
Wide Range ◽  
Lower Temperature ◽  
Sulfide Contraction

A wide range of N-(ethoxycarbonylmethyl)enaminones, prepared by the Eschenmoser sulfide contraction between N-(ethoxycarbonylmethyl)pyrrolidine-2-thione and various bromomethyl aryl and heteroaryl ketones, underwent cyclization in the presence of silica gel to give ethyl 6-(hetero)aryl-2,3-dihydro-1H-pyrrolizine-5-carboxylates within minutes upon microwave heating in xylene at 150 °C. Instead of functioning as a nucleophile, the enaminone acted as an electrophile at its carbonyl group during the cyclization. Yields of the bicyclic products were generally above 75%. The analogous microwave-assisted reaction to produce ethyl 2-aryl-5,6,7,8-tetrahydroindolizine-3-carboxylates from (E)-ethyl 2-[2-(2-oxo-2-arylethylidene)piperidin-1-yl]acetates failed in nonpolar solvents, but occurred in ethanol at lower temperature and microwave power, although requiring much longer time. A possible mechanism for the cyclization is presented, and further functionalization of the newly created pyrrole ring in the dihydropyrrolizine core is described.

STUDY OF THE ESCHENMOSER SULFIDE CONTRACTION METHOD WITH AND WITHOUT A THIOPHILE

1992 ◽  
Vol 71 (1-4) ◽  
pp. 197-206 ◽  
Author(s):  
A. Corsaro ◽  
G. Perrini ◽  
M. G. Testa ◽  
U. Chiacchio
Keyword(s):  
Contraction Method ◽  
Sulfide Contraction

ChemInform Abstract: The Eschenmoser Sulfide Contraction Method and Its Application in the Synthesis of Natural Products

ChemInform ◽  
2015 ◽  
Vol 46 (38) ◽  
pp. no-no ◽  
Author(s):  
Syed Raziullah Hussaini ◽  
Raghu Ram Chamala ◽  
Zhiguo Wang
Keyword(s):  
Natural Products ◽  
Contraction Method ◽  
Sulfide Contraction
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