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  • P-ISSN2233-4203
  • E-ISSN2093-8950

Observations on Fragmentation Pathway of Farinomalein and its Isomers by Structural Investigation Using LC-MS/MS

Mass Spectrometry Letters, (P)2233-4203; (E)2093-8950
2018, v.9 no.1, pp.37-40
https://doi.org/10.5478/MSL.2018.9.1.37
Narayan P. Firke (Affiliated to Shivaji University)
Anil G. Markandeya (Affiliated to Savitribai Phule Pune University)
Rajendra S. Konde Deshmukh (Affiliated to Savitribai Phule Pune University)
Shirish S. Pingale (Affiliated to Savitribai Phule Pune University)
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Abstract

Farinomalein is a maleimide-bearing compound well known for its anti-fungal activity. In the present study, synthesis of farinomalein is achieved via Stobbe condensation followed by Haval-Argade contrathermodynamic rearrangement. Kinetically driven Stobbe condensation followed by condensation with beta-alanine reveals formation of two isomers of farinomalein. This article describes application of LC-MS/MS in structure elucidation of farinomalein 1 and its isomers 2 and 3 encountered in its synthesis. The proposed distinct fragmentation pathway is supported by rational organic reaction mechanism. These fragmentation pathways are significant for analytical method development of farinomalein in near future. The structures of farinomalein 1 and its isomers 2 and 3 have been assigned undisputedly.

Submission Date
2017-11-21
Revised Date
2017-12-27
Accepted Date
2018-01-10

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Mass Spectrometry Letters