Pyrrol inones

MDPF is closely related in structure to fluorescamine. Both primary and secondary amines react with MDPF in acetonitrile, but only primary amines form fluorescent pyrrol inones. Secondary amines form non-fluorescent aminodienones. By reacting with ethanolamine, the latter produce fluorescent products. Their stability is adequate for chromatographic separation [258, 259]. 

HydroxyNPYR [ ] has been identified as a urinary metabolite of NPYR in the rat (up to 1% of the dose), but was not detected when NPYR was incubated with subcellular fractions from rat liver and lung (13, 20). It has been proposed that further metabolism of leads to dimethy 1 amine, [ ], another urinary metabolite of NPYR, 2-Pyrrolidinone [3 ] has also been detected in the urine of rats treated with NPYR. Its origin has not been conclusively established, but it may form from pyrrol id inone-2-oxime (i6). 

Efficient domino approaches to multifunctionalized tricyclic fused pyrroles 59 and dibenzo[h,e][l,4]diazepin-l-ones 60 have been established starting from enam-inones 57 with different substitution patterns and arylglyoxal monohydrates 58. The reaction pathway is controlled by the substituent at the N atom in 57. The domino process can easily be performed by simply mixing 58 and N-amino acid enaminones or 3-(2-aminophenylamino)-5,5-dimethylcyclohex-2-enones 57 in the presence of AcOH under microwave irradiation (Scheme 12.21). The reaction occurs within 12-36 min, with water as the second product. A complete anti diastereoselectivity was achieved within the formation of tricyclic fused pyrrole derivatives [42]. 

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