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Synthesis of 2‐Cyanoquinazolin‐4‐ones from 3′,5′‐Dichloro‐1 H ‐spiro(quinazoline‐2,4′‐[1,2,6]thiadiazin)‐4(3 H )‐ones
Author(s) -
Kalogirou Andreas S.,
Kourtellaris Andreas,
Koutentis Panayiotis A.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000137
Subject(s) - triphenylphosphine , quinazoline , iodide , chemistry , medicinal chemistry , stereochemistry , catalysis , organic chemistry
A two‐step synthesis of five 2‐cyanoquinazolin‐4‐ones starting from 3,4,4,5‐tetrachloro‐4 H ‐1,2,6‐thiadiazine is presented. The latter reacts with 2‐aminobenzamides to give 3′,5′‐dichloro‐1 H ‐spiro(quinazoline‐2,4′‐[1,2,6]thiadiazin)‐4(3 H )‐ones, which can be degraded with either excess polymer bound triphenylphosphine or catalytic amounts of benzyltriethylammonium iodide to give the 2‐cyanoquinazolin‐4‐ones in 46–97% yields. The single crystal X‐ray diffraction analysis of 2‐cyanoquinazolin‐4(3 H )‐one is also reported.