An Unprecedented Pseudo-[3+2] Annulation between N-(4-Methoxyphenyl)aldimines and Aqueous Glutaraldehyde: Direct Synthesis of Pyrrole-2,4-dialdehydes

作者：Ramaraju Panduga; Mir Nisar A; Singh Deepika; Sharma Preetika; Kant Rajni; Kumar Indresh^*

来源：European Journal of Organic Chemistry, 2017, 2017(24): 3461-3465.

DOI：10.1002/ejoc.201700500

• Aldehydes
• Imines
• Organocatalysis
• Mannich reaction
• Nitrogen heterocycles

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 %).

• 出版日期2017-6-30