51671-83-1Relevant academic research and scientific papers
Regioselective synthesis of 5-unsubstituted benzyl pyrrole-2-carboxylates from benzyl isocyanoacetate
Ono,Katayama,Nisyiyama,Ogawa
, p. 707 - 710 (2007/10/02)
A general synthesis of 5-unsubstituted benzyl pyrrole-2-carboxylates was developed based on the reaction of β-nitroacetates with benzyl isocyanoacetate. The advantage of this route over other pyrrole syntheses was the regiochemical control of the substitution pattern on the pyrrole ring.
Synthesis of pyrroles from benzyl isocyanoacetate
Lash,Bellettini,Bastian,Couch
, p. 170 - 172 (2007/10/02)
Benzyl esters of 5-unsubstituted pyrrole-2-carboxylic acids were prepared in excellent yields by the base-catalyzed condensation of benzyl isocyanoacetate with α-acetoxynitro compounds, or nitro-alkenes, in refluxing tetrahydrofuran. These pyrrolic products are important intermediates in the synthesis of porphyrins and related compounds.
Synthesis of Benzyl and tert-Butyl 3-(2-Methoxycarbonylethyl)-4-methylpyrrole-2-carboxylates from Methyl 4-Oxobutanoate
Drinan, Martin A.,Lash, Timothy D.
, p. 255 - 258 (2007/10/02)
Condensation of methyl 4-oxobutanoate with nitroethane in the presence of 4-dimethylaminopyridine, followed by treatment with acetic anhydride, afforded a nitroacetoxyester 10b.Subsequent reaction with isocyanoacetate esters and DBU in refluxing tetrahydrofuran gave the synthetically valuable pyrroles 1a and 1b.
Synthetic and Biosynthetic Studies of Porphyrins. Part 7. The Action of Coproporphyrinogen Oxidase on Coproporphyrinogen-IV: Syntheses of Protoporphyrin-XIII, Mesoporphyrin XIII, and Related Tricarboxylic Porphyrins
Al-Hazimi, Hassan M. G.,Jackson, Anthony H.,Knight, David W.,Lash, Timothy D.
, p. 265 - 276 (2007/10/02)
Coproporphyrinogen-IV (2a) is converted by an enzyme system from chicken blood into a tricarboxylic porphyrinogen (2b) and protoporphyrinogen-XIII (2c).The corresponding porphyrins were isolated as their methyl esters (3b) and (3c) and their structures were deduced by mass and n.m.r. spectrometry (including the use of shift reagents).Confirmation of these conclusions was obtained by total synthesis of the new porphyrins by the MacDonald and ac-biladiene routes.The vinyl groups were introduced either via acetoxyethyl side-chains derived from precursor pyrroles, or by reduction and dehydration of acetyl groups inserted into the porphyrins during the final stages of the syntheses.Mesoporphyrin-XIII dimethyl ester (3m) and the ethyl analogue (3n) of the vinyl tripropionate porphyrin (3b) were also synthesized by the MacDonald route.
Biosynthesis of Porphyrins and Related Macrocycles. Part 25. Synthesis of Analogues of Coproporphyrinogen-III and Studies of their Interaction with Copropophyrinogen-III Oxidase from Euglena gracilis
Robinson, John A.,McDonald, Edward,Battersby, Alan R.
, p. 1699 - 1710 (2007/10/02)
Analogues of coproporphyrinogen-III have been synthesized in which the propionate groups respectively on ring-A and on ring-B are modified either by homologation or esterification.Coproporphyrinogen-III oxidase from Euglena gracilis acts on the analogues which possess normal substituents on ring-A to generate a vinyl group on that ring.The enzyme does not affect the analogues in which the ring-A propionate group has been changed.Conditions have been defined for the MacDonald synthesis of porphyrins which yield products of high isomeric purity.
BILE PIGMENT STUDIES - VII NEW SYNTHESES OF BILIVERDIN-IXα DIMETHYL ESTER AND TWO RELATED MONO-VINYL-ETHYL ISOMERS
Smith, Kevin M.,Pandey, Ravindra K.
, p. 1749 - 1754 (2007/10/02)
Using the recently developed route through di-t-butyl b-bilene-1,19-dicarboxylates, new syntheses of biliverdin-IXα dimethyl ester (1) and two related mono-vinyl-mono-ethyl isomers (2) and (3), are described.The two dihydro-derivatives of (1) are importan
