112373-38-3

Basic information

• Product Name: C₁₇H₁₈N₄O₄S
• Synonyms: C₁₇H₁₈N₄O₄S
• CAS NO: 112373-38-3
• Molecular Weight: 374.42
• Mol File: 112373-38-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₇H₁₈N₄O₄S(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₇H₁₈N₄O₄S(112373-38-3)
• EPA Substance Registry System: C₁₇H₁₈N₄O₄S(112373-38-3)

Safety Data

• Hazardous Substances Data: 112373-38-3(Hazardous Substances Data)

Upstream product

• 112373-16-7 4,5-diiodo-3-methoxy-2-(methoxycarbonyl)pyrrole 
• 112373-17-8 3-methoxy-2-(methoxycarbonyl)pyrrole 
• 112373-19-0 4-methoxy-5-(methoxycarbonyl)-1,1'-carbonyl-2,2'-bipyrrole 
• 112373-18-9 3-methoxy-2-(methoxycarbonyl)-1,1'-carbonyldipyrrole 
• 112373-36-1 4-methoxy-5-(methoxycarbonyl)-2,2'-bipyrrole 
• 325460-96-6 4-methoxy-1H,1'H-[2,2']bipyrrolyl-5-carboxylic acid tert-butyl ester 
• 182818-88-8 3-methoxypyrrole-2-carboxylic acid tert-butyl ester 
• 112373-37-2 4-Methoxy-1H,1'H-[2,2']bipyrrolyl-5-carboxylic acid hydrazide 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 82-89-3 4-methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1'H-2,2'-bipyrrole 
• 52340-48-4 undecylprodigiosin 
• 10476-41-2 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde 

Relevant articles and documents

Pyrrole-singlet oxygen reactions leading to α,α'-bipyrroles. Synthesis of prodigiosin and analogs

Reaction of the tert-butyl ester of 3-methoxy-2-pyrrolecarboxylic acid with singlet oxygen yields a hydroperoxide intermediate which undergoes coupling with pyrroles to yield precursors of prodigiosin and ring A analogs, readily convertible to the corresponding tripyrromethenes.

TOTAL SYNTHESIS OF PRODIGIOSIN

The total synthesis of prodigiosin (1), possessing the characteristic pyrrolylpyrromethene skeleton of a class of naturally-occuring polypyrroles, is detailed.The approach is based on the application of an inverse electron demand Diels-Alder reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate in a 1,2,4,5-tetrazine -> 1,2-diazine -> pyrrole strategy for preparation of prodigiosin pyrrole ring B and the subsequent implementation of an intramolecular palladium(II)-promoted 2,2'-diaryl (2,2'-bipyrrole) coupling for construction of the prodigiosin 2,2'-bipyrrole AB ring system.