Journal of Food, Agriculture and Environment

Synthesis of new 2,5-dimethyl pyrrole derivatives and their application in unblended cigarette 

Author(s):

Xiao Ming Ji, Ming Qin Zhao*, Yue Zhang, Xiao Yun Zhang, Ye Lu

Recieved Date: 2012-04-18, Accepted Date: 2013-01-21

Abstract:

Acetylacetone 1 was treated with  bromine oxidant in anhydrous tetrahydrofuran to give 3,4-diacetyl-2,5-hexanedione 2 by cross-coupling reaction, then 2 was successfully transformed into the related pyrrole derivative 3,4,5,6 by Paal-Knorr reaction with thiourea, thiosemicarbazide, glycine and glutamic acid. N-dimethyl pyrrole acids 8 and 9 were synthesized and characterized by 2,5-hexanedione 7, then N-dimethyl pyrrole ester 10, 11, 12 and 13 were obtained by reacting 8 and 9 with benzene alcohol, benzyl alcohol and menthol by esterification reactions, respectively. The structures of all new products were elucidated by IR, ¹H NMR, ¹³C NMR and HRMS spectra, and the applications of the compounds to unblended cigarette flavoring were studied as well. Those target compounds were beneficial to the smell of tobacco flavor, characterized by enhancing the aroma quality and volume of aroma, reducing irritancy and improving the aftertaste. 

Keywords:

2,5 -dimethyl pyrrole derivatives, synthesis, application, unblended cigarette

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Journal: Journal of Food, Agriculture and Environment
Year: 2013
Volume: 11
Issue: 1
Category: Environment
Pages: 902-905

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