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An Unprecedented Pseudo‐[3+2] Annulation between N ‐(4‐Methoxyphenyl)aldimines and Aqueous Glutaraldehyde: Direct Synthesis of Pyrrole‐2,4‐dialdehydes
Author(s) -
Ramaraju Panduga,
Mir Nisar A.,
Singh Deepika,
Sharma Preetika,
Kant Rajni,
Kumar Indresh
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700500
Subject(s) - aldimine , chemistry , annulation , pyrrole , glutaraldehyde , mannich reaction , aqueous solution , organic chemistry , combinatorial chemistry , catalysis
A new method for the direct one‐pot synthesis of substituted pyrrole‐2,4‐dialdehdyes was developed. This overall pseudo‐[3+2]‐annulation reaction between glutaraldehyde and N ‐(4‐methoxyphenyl)aldimines proceeds through proline‐catalyzed direct Mannich reaction/cyclization, followed by 2‐iodoxybenzoic acid mediated oxidative rearrangement of the in situ generated intermediate to give pyrrole‐2,4‐dialdehydes in high yields (up to 80 %).