Diferrocenyl(hydroxy)oxazepines and diferrocenyl-4-aza-1,3-dienes in the reactions of 2,3-diferrocenyl-1-methylthiocyclopropenylium iodide with aromatic and aliphatic bis-1,4-N,O-nucleophiles

Add time:08/25/2019    Source:sciencedirect.com

A novel method for the synthesis of 3,4-diferrocenyl-2-methylthio-2,3-dihydrobenzo[b]-1,4-oxazepin-3-ols 7a-e (23-30%), 3,4-diferrocenylquinolin-8-ols 8b-d (9-16%), 1-E-2,3-diferrocenyl-4-(2-hydroxyphenyl)-1-methylthio-4-aza-1,3-dienes 9a-e (24-30%), cis-/trans-2,3-diferrocenyl-3-methylthioacroleins 10a,b (7-19%), S,R-5,6-diferrocenyl-7-methylthio-2,3,6,7-tetrahydro-1,4-oxazepin-6-ols 13b,d,e (28-33%) and E,Z- and Z,E-2,3-diferrocenyl-6-hydroxy-1-methylthio-4-aza-1,3-alkadienes 14a-e (29-34%) and 15a-e (10-13%) by reactions of 2,3-diferrocenyl-1-sulfanyl-cyclopropenylium iodide 2 with aromatic and aliphatic bis-1,4-N,O-nucleophiles (1,2-aminophenols 3a-e and 1,2-aminoalcohols 11a-e) in the presence of Et3N is presented. A new reaction for the transformation of the intermediate products of the addition of bis-1,4-N,O-nucleophiles 3a-e and 11a-e to the diferrocenylciclopropenilium cation 2 in the positions C(1) and C(2) is found. The characterization of the new compounds was conducted by IR, 1H- and 13C-NMR spectroscopy, mass-spectrometry, elemental analysis, and X-ray diffraction.

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