Regioselective Synthesis of the 5,6‐Dihydro‐4 H ‐furo[2,3‐ c ]pyrrol‐4‐one Skeleton: A New Class of Compounds | Zendy

Koza Gani | Zendy; Karahan Emrah | Zendy; Balci Metin | Zendy

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Regioselective Synthesis of the 5,6‐Dihydro‐4 H ‐furo[2,3‐ c ]pyrrol‐4‐one Skeleton: A New Class of Compounds

Author(s) -

Koza Gani,

Karahan Emrah,

Balci Metin

Publication year - 2010

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200900448

Subject(s) - chemistry , curtius rearrangement , regioselectivity , intramolecular force , nucleophile , amine gas treating , derivative (finance) , azide , isocyanate , methylene , medicinal chemistry , furan , protecting group , organic chemistry , stereochemistry , catalysis , alkyl , financial economics , economics , polyurethane

We hereby report the first preparation of the 5,6‐dihydro‐4 H ‐furo[2,3‐ c ]pyrrol‐4‐one ( 3 ) and its derivatives starting from methyl 3‐(methoxycarbonyl)furan‐2‐acetate ( 8 ). The ester functionality connected to the methylene group was regiospecifically converted to the desired monohydrazide 9 . Conversion of 9 into the acyl azide 10 followed by Curtius rearrangement gave the corresponding isocyanate derivative 11 ( Scheme 2 ). Reaction of 11 with different nucleophiles produced urethane and urea derivatives ( Scheme 3 ). Intramolecular cyclization reactions provided the target compounds ( Scheme 5 ). Removal of the amine‐protecting group formed the title compound 3 .

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