Journal
TETRAHEDRON LETTERS
Volume 60, Issue 46, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2019.151247
Keywords
Mannich reaction; Pyrrole; Diamine; Macrocycle
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Funding
- DST
- CSIR (New Delhi, India)
- DST FIST Level -II grant [SR/FST/CSII026/2013]
- IIT Kharagpur
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The Mannich reaction of pyrrole with ethylenediamine dihydrochloride and formaldehyde gave two compounds: N-1,N-1,N-2,N-2-tetrakis(pyrrol-2-ylmethyl)ethane-1,2-diamine 1 and 1,3-bis(pyrrol-2-ylmethyl)imidazolidine 2 in poor yields. Conversely, the reaction of pyrrole with propylenediamine dihydrochloride afforded macrocyclic compound 3 containing two pyrrole rings bridged by two dimethylenehexahy-dropyrimidine moieties in 50% yield. The reaction of 2,5-dimethylpyrrole with methylamine hydrochloride and formaldehyde gave novel bicycle 4 consisting of a dimethyltetrahydro-1,3-diazepine ring fused with a 2,5-dimethylpyrrole ring. The reaction of 2,5-dimethylpyrrole with ammonium chloride gave the tripodal ligand tris(2,5-dimethylpyrrol-3-yl)methylamine 5 in 62% yield. The structures of 2-4 were determined by single crystal X-ray diffraction studies. (C) 2019 Elsevier Ltd. All rights reserved.
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