104208-14-2

Usage

Synthesis Reference(s)

Tetrahedron, 41, p. 3803, 1985 DOI: 10.1016/S0040-4020(01)91401-2

InChI:InChI=1/C9H14N2O/c1-10-5-6-11(2)9(10)8-4-3-7-12-8/h3-4,7,9H,5-6H2,1-2H3

Upstream product

• 98-01-1 furfural 
• 110-70-3 N,N`-dimethylethylenediamine 

Downstream Products

• 620-02-0 5-Methylfurfural 
• 13529-17-4 5-Formyl-2-furancarboxylic acid 
• 13529-06-1 (5-trimethylsilanyl)furan-2-carbaldehyde 
• 823-82-5 2,5-diformylfurane 
• 13529-18-5 5-benzoyl-furan-2-carbaldehyde 

Relevant academic research and scientific papers

Rediscovering aminal chemistry: Copper(ii) catalysed formation under mild conditions

Aminals, the N,N analogues of acetals, have been thoroughly explored in organic chemistry, with a particular focus on heteroaromatic aldehyde lithiation. Nevertheless, the existing methodologies for their formation typically employ harsh conditions limiting their usefulness. In this work, we present an efficient and mild methodology for the preparation of aminals from aromatic aldehydes, including furanic platforms. These mild conditions allowed ease of access to a plethora of aminals and as such we set out to explore previously unaccessible potential applications. By studying the stability of various aminals, we were able to develop a simple aldehyde protecting group based on a commercial diamine which is deprotected under mind conditions. We developed a protocol for the scavenging of genotoxic aldehydes by taking advantage of our methodology and a diamine resin, as well as early studies on the development of a stimuli-responsive release system using a salycil aldehyde derived aminal. This journal is

NOVEL INHIBITORS OF FRUCTOSE 1,6-BISPHOSPHATASE

The invention relates to compounds of Formula I-III and IX-XIII, their prodrugs and salts and co-crystals thereof. The invention further relates to process and methods of making and using the same.

Combination of FBPase inhibitors and insulin sensitizers for the treatment of diabetes

Pharmaceutical compositions containing an FBPase inhibitor and an insulin sensitizer are provided as well as methods for treating diabetes and diseases responding to increased glycemic control, an improvement in insulin sensitivity, a reduction in insulin levels, or an enhancement of insulin secretion.

Combination of FBPase inhibitors and antidiabetic agents useful for the treatment of diabetes

A combination therapy of at least one FBPase inhibitor and at least one other antidiabetic agent is disclosed.

Novel bisamidate phosphonate prodrugs

Novel bisamidate phosphonate prodrugs of FBPase inhibitors of the Formula IA: and their use in the treatment of diabetes and other conditions associated with elevated blood glucose.

Heteroaromatic compounds containing a phosphonate group that are inhibitors of fructose-1,6-bisphosphatase

FBPase inhibitors of the formula I and X are useful in the treatment of diabetes and other conditions associated with elevated blood glucose or excess glycogen storage.

Purine inhibitors of fructose 1,6-bisphosphatase

Novel purine compounds of the following structure and their use as fructose-1,6-bisphosphatase inhibitors is described. wherein A is selected from the group consisting of —NR82, —NHSO2R3, —OR5, —SR5, halo, lower alkyl, —CON(R4)2, guanidino, amidino, —H, and perhaloalkyl; E is selected from the group consisting of —H, halo, lower alkylthio, lower perhaloalkyl, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, —CN, and —NR72; X is selected from the group consisting of -alk-NR—, alkylene, alkenylene, alkynylene, arylene, heteroarylene, -alk-NR-alk-, -alk-O-alk-, -alk-S-alk-, -alk-S—, alicyclicene, heteroalicyclicene,1,1-dihaloalkylene, —C(O)-alk-, —NR—C(O)—NR′—, -alk-NR—C(O)—, -alk-C(O)—NR—, —Ar-alk-, and -alk-Ar—, all optionally substituted, wherein each R and R′ is independently selected from —H and lower alkyl, and wherein each “alk” and “Ar” is an independently selected alkylene or arylene, respectively; Y is selected from the group consisting of —H, alkyl, alkenyl, alkynyl, aryl, alicyclic, heteroalicyclic, aralkyl, aryloxyalkyl, alkoxyalkyl, —C(O)R3, —S(O)2R3, —C(O)—OR3, —CONHR3, —NR22, and —OR3, all except H are optionally substituted; and pharmaceutically acceptable prodrugs and salts thereof.

CHEMOSELECTIVE PROTECTION OF HETEROAROMATIC ALDEHYDES AS IMIDAZOLIDINE DERIVATIVES. PREPARATION OF 5-SUBSTITUTED FURAN- AND TIOPHENE-2-CARBOXALDEHYDES VIA METALLO-IMIDAZOLIDINE INTERMEDIATES

Furan-, tiophene- and N-methylpyrrole-2-carboxaldehydes may be transformed into the corresponding N,N'-dimethylimidazolidines in a reaction not requiring acid catalysis.The resulting furan and tiophene (but not N-methylpyrrole) derivatives may be metallated in high yields and the carboxaldehyde functionality regenerated under very mild conditions.Treatment of the aldehydoketone 2-acetyl-5-formylthiophene with N,N'-dimethylethylenediamine gives only the product of reaction at the aldehyde function thus establishing this methodology as a potentially valuable method for the protection of an aldehyde in the presence of a ketone.