scholarly journals The Birch Reduction of Heterocyclic Carboxylic Acids. I. The Birch Reduction of 3-Furoic Acid

1975 ◽  
Vol 48 (6) ◽  
pp. 1865-1867 ◽  
Author(s):  
Takamasa Kinoshita ◽  
Kouichi Miyano ◽  
Toshio Miwa
Keyword(s):  
Carboxylic Acids ◽  
Furoic Acid ◽  
Birch Reduction

ChemInform Abstract: Stereoselectivity in the Birch Reduction of 2-Furoic Acid Derivatives.

ChemInform ◽  
2010 ◽  
Vol 29 (31) ◽  
pp. no-no
Author(s):  
T. J. DONOHOE ◽  
M. HELLIWELL ◽  
C. A. STEVENSON ◽  
T. LADDUWAHETTY
Keyword(s):  
Furoic Acid ◽  
Birch Reduction

Stereoselectivity in the Birch reduction of 2-furoic acid derivatives

1998 ◽  
Vol 39 (19) ◽  
pp. 3071-3074 ◽  
Author(s):  
Timothy J Donohoe ◽  
Madeleine Helliwell ◽  
Clare A Stevenson ◽  
Tamara Ladduwahetty
Keyword(s):  
Furoic Acid ◽  
Birch Reduction

Heteroaromatics: The Mal Synthesis of Clausevatine D

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Carboxylic Acids ◽  
South China ◽  
University Of Illinois ◽  
Dicarbonyl Compound ◽  
Furoic Acid ◽  
University Of Technology ◽  
Decarboxylative Coupling ◽  
National University ◽  
La Jolla ◽  
The University

Huanfeng Jiang of the South China University of Technology showed (J. Org. Chem. 2010, 75, 966) that an alkynoate 1 could be condensed with a 1,3-dicarbonyl compound 2 to give, under oxidizing conditions, the furan 3. Phil Ho Lee of Kangwon National University found (Tetrahedron Lett. 2010, 51, 1899) that the enyne 4 cyclized smoothly to the furan 5. Yahong Li of Suzhou University and Vladimir Gevorgyan of the University of Illinois, Chicago, demonstrated (J. Am. Chem. Soc. 2010, 132, 7645) that the cyclization of 6 proceeded with silyl migration, to give 7. François Bilodeau and Pat Forgione of Boehringer Ingelheim (Canada) optimized (J. Org. Chem. 2010, 75, 1550) the Pd-mediated decarboxylative coupling of a furoic acid 8 with 9 to give 10. This protocol also worked well with pyrrole carboxylic acids. In another transformation of a preformed pyrrole, Masatomo Iwao of Nagasaki University observed (Organic Lett. 2010, 12, 2734) that in the presence of LDA/diisopropylamine, the initially formed 2-anion from the deprotonation of 11 gave the 2-product 12 with more reactive electrophiles but the 5-product 13 with less reactive electrophiles. Umasish Jana of Jadavpur University developed (J. Org. Chem. 2010, 75, 1674) a route to more highly substituted pyrroles such as 17 using the remarkable four-component coupling of 14, 15, and 16 with nitromethane, the carbon of which was incorporated in the product. Laura L. Anderson, also of the University of Illinois, Chicago, designed (Organic Lett. 2010, 12, 2290) a clever approach to pyrroles, based on the Ir-catalyzed rearrangement of O-allyl oximes such as 18. Xiaofeng Tong of the East China University of Science and Technology reported (Chem. Commun. 2010, 312) the condensation of 20 with 21 to give the dihydropyridine 22. Base-mediated elimination of sulfinate could convert 22 into the pyridine. Jin-Quan Yu of Scripps/La Jolla found (Angew. Chem. Int. Ed. 2010, 49, 1275) that Pd-mediated activation of the nictotinamide 23 proceeded with high regioselectivity, leading to 25. Zhiping Li of Remnin University of China demonstrated (J. Org. Chem. 2010, 75, 4636) that the chloroenamine 26 cyclized to the indole 27 on exposure to NaI.

Evidence for a Trianion Intermediate in the Birch Reduction of Aromatic Carboxylic Acids

1981 ◽  
Vol 11 (3) ◽  
pp. 223-229 ◽  
Author(s):  
A. Casares ◽  
J. M. L. Cardoso ◽  
L. A. Maldonado
Keyword(s):  
Carboxylic Acids ◽  
Birch Reduction ◽  
Aromatic Carboxylic Acids

PERMANGANATE–PERIODATE OXIDATION: VI. THE OXIDATION OF VARIOUS ALIPHATIC COMPOUNDS

1965 ◽  
Vol 43 (6) ◽  
pp. 1784-1791 ◽  
Author(s):  
E. Von Rudloff
Keyword(s):  
Succinic Acid ◽  
Tartaric Acid ◽  
Carboxylic Acids ◽  
Propionic Acid ◽  
Ethyl Acetoacetate ◽  
Periodate Oxidation ◽  
Furoic Acid ◽  
Aliphatic Compounds ◽  
End Products ◽  
Oxalic Acids

A study was made of the reaction of the permanganate–periodate reagent with a wide variety of aliphatic alcohols, polyols, aldehydes, acids, oxy-acids, ketones, ethers, and esters. Saturated monols, ketones, and ethers, as well as acetic, pelargonic, pyruvic, lactic, and oxalic acids reacted only very slowly. Glycols, olefinic alcohols, and unsaturated acids were cleaved to give predictable end products. Activated alcohols and ethyl acetoacetate reacted at relatively high rates. Formic, glyoxylic, lactic, and malonic acids as well as 1,3-propanediol and 2,5-hexane dione reacted extensively and diethyl tartrate consumed as much oxidant as did tartaric acid. The oxidation of tetrahydrofurfuryl alcohol gave succinic acid instead of the expected tetrahydro-2-furoic acid. Saturated mono- and di-carboxylic acids, 3-hydroxy propionic acid, γ-valero lactone, and saturated esters were stable towards the reagent.

Sign in / Sign up

Export Citation Format

Share Document