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Functionalized Pyrimidines from Alkynes and Nitriles: Application towards the Synthesis of Marine Natural Product Meridianin Analogs
Author(s) -
Mohan Banyangala,
Salfeena Chettiyan Thodi F.,
Ashitha Kizhakkan T.,
Krishnan Gopika V.,
Jesmina Abdul Rasheed S.,
Varghese Angela M.,
Patil Siddappa A.,
Kumar Bhaskaran Nair S. Dileep,
Sasidhar Balappa S.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801126
Subject(s) - natural product , chemistry , cycloaddition , nitrile , pyrimidine , broad spectrum , combinatorial chemistry , substrate (aquarium) , stereochemistry , organic chemistry , catalysis , biology , ecology
Fully substituted pyrimidine synthesis accomplished from alkynes and nitriles via BF 3 . Et 2 O mediated [2+2+2] cycloaddition. The substrate scope of the reaction was broad to include terminal alkynes to internal alkynes and aromatic nitriles to aliphatic nitriles furnished good to acceptable chemical yields. The marine alkaloid, meridianin analogs were synthesized successfully by utilizing this protocol. The pyrimidine analogues were also screened for their broad spectrum of antibacterial property against ten bacteria. Among the derivatives, 2,4‐dimethyl‐6‐ p ‐tolylpyrimidine ( 3b ) has shown excellent inhibition potential against most of the tested organisms with a range of 9 to 21 mm zone of inhibition.