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Synthesis of New N ‐alkyl‐5‐formyl‐2‐methylpyrrole Derivatives from Glucosamine
Author(s) -
Tao Tao,
Zhao Hua Xin,
Ji Xiao Ming,
Lai Miao,
Zhao Ming Qin
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3122
Subject(s) - chemistry , pyrrole , alkylation , glucosamine , hydrochloride , d glucosamine , alkyl , derivative (finance) , medicinal chemistry , organic chemistry , catalysis , financial economics , economics
Glucosamine hydrochloride 1 was treated with 1,3‐dicarbonyl compounds to obtain 2‐methyl‐5‐(1,2,3,4‐tetrahydroxy‐butyl) pyrrole 2a and 2b , respectively. Under the role of NaIO 4 , 2a and 2b were successfully transformed into the related 5‐formal pyrrole derivative 3a and 3b , respectively. Compounds 4a – 4d and 5a – 5e were obtained by reacting 3a and 3b with chlorinated hydrocarbons by alkylation reactions, respectively. The structures of all new products were confirmed by IR, NMR, and HRMS spectra.