31896-88-5Relevant articles and documents
Deiodination of 5-iodopyrrole-2-carboxylates using sodium formate catalyzed by palladium complexes: Preparation of 5-unsubstituted pyrrole-2-carboxylates
Leung, Sam H.,Edington, Daniel G.,Griffith, Tara E.,James, Jammie J.
, p. 7189 - 7191 (1999)
5-Iodopyrrole-2-carboxylates are deiodinated with sodium formate in the presence of a catalytic amount of either PdCl2(Ph3P)2 or Pd(Ph3P)4 to give the corresponding 5-unsubstituted pyrrole-2-carboxyla
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.
Porphyrins with Exocyclic Rings. Part 3. A Reassessment on the Utility of Cyclopentapyrroles in the Synthesis of Porphyrin Molecular Fossils. Preparation of Three Type II Porphyrins Related to Deoxophylloerythroetioporphyrin (DPEP)
Lash, Timothy D.,Catarello, James J.
, p. 4159 - 4172 (2007/10/02)
The utility of cyclopentapyrroles in porphyrin synthesis has been reinvestigated.A 6-oxocyclopentapyrrole 18 was prepared by cyclization of the propanoyl chloride sidechain of an α-unsubstituted pyrrole 17d in the presence of tin(IV) chloride.Subsequent reduction with sodium borohydride afforded the corresponding 6-hydroxy compound 10 and further acid catalyzed condensation with α-unsubstituted pyrroles 11a and 11b gave the novel 6-pyrrolylcyclopentapyrroles 22a and 22b in excellent yields.Attempts to prepare deoxophylloerythroetioporphyrin (DPEP; 2), a widespread sedimentary porphyrin molecular fossil, from these dipyrrolic intermediates using the tripyrrene-a,c-biladiene route were unsuccessful.However, the synthesis of three related meso,β-ethanoporphyrins using the MacDonald condensation was successfully carried out in moderate to good yields.Retention of an sp3 hybridized carbon bridge at the cyclopentene ring fusion site of the intermediary open chain tetrapyrroles appears to be crucial during macrocycle formation, as this diminishes the steric repulsion between the peripheral substituents and the carbocyclic ring.