Efficient synthesis of racemic β-aminophosphonates via aza-Michael reaction in water

Design, cytotoxic and fluorescent properties of novel N-phosphorylalkyl substituted E,E-3,5-bis(arylidene)piperid-4-ones

“…According to our data [31], water as a solvent significantly accelerates the addition of various amines to diethoxyvinylphosphonate to yield b-aminophosphonates without any catalyst compared to other known procedures for this reaction. When 4-piperidone hydrochloride was used as a starting amine b-aminophosphonate 5a was isolated in 62% yield after purification by chromatography.…”

“…19 (C(6) and C(6 0 )), 147.42 (C(9) and C(9 0 ), 185.88 (C(O)). 31 (8), C(10), C(8 0 ), C(10 0 )), 123.10 (C(6) and C(6 0 )), 129.03 (C(3) and C(3 0 )), 132.27 (C(7), C(11), C(7 0 ), C(11 0 )), 136.30 (C(5) and C(5 0 )), 150.33 (C(9) and C(9 0 )), 186.76 (C(O)). 31 4)).…”

“…31 (8), C(10), C(8 0 ), C(10 0 )), 123.10 (C(6) and C(6 0 )), 129.03 (C(3) and C(3 0 )), 132.27 (C(7), C(11), C(7 0 ), C(11 0 )), 136.30 (C(5) and C(5 0 )), 150.33 (C(9) and C(9 0 )), 186.76 (C(O)). 31 4)). 19 (8), C(10), C(8 0 ), C(10 0 )), 130.60 (C(7), C(11), C(7 0 ), C(11 0 )), 133.78 (C(5) and C(5 0 )), 135.52 (C(3) and C(3 0 )), 140.99 (C(6) and C(6 0 )), 147.28 (C(9) and C(9 0 )), 186.10 (C(O)).…”

“…19 (8), C(10), C(8 0 ), C(10 0 )), 130.60 (C(7), C(11), C(7 0 ), C(11 0 )), 133.78 (C(5) and C(5 0 )), 135.52 (C(3) and C(3 0 )), 140.99 (C(6) and C(6 0 )), 147.28 (C(9) and C(9 0 )), 186.10 (C(O)). 31 (8), C(10), C(8 0 ), C(10 0 )), 123.04 (C(6) and C(6 0 )), 128.98 (C(3) and C(3 0 )), 132.09 (C(7), C(11), C(7 0 ), C(11 0 )), 136.10 (C(5) and C(5 0 )), 150.13 (C (9) and C(9 0 )), 186.63 (C(O)). 31 3 J CP ¼ 16.1 Hz), 54.36 (N(CH 2 ) 2 cyclic), 56.44 (NCH 2 CH 2 CH 2 CH 2 P), 61.21 (d, POCH 2 CH 3 , 2 J CP ¼ 6.2 Hz), 123.60 (C(8), C(10), C(8 0 ), C(10 0 )), 130.62 (C(7), C(11), C(7 0 ), C(11 0 )), 133.79 (C(5) and C(5 0 )), 135.63 (C(3) and C(3 0 )), 141.08 (C(6) and C(6 0 )), 147.31 (C(9) and C(9 0 )), 186.19 (C(O)).…”

“…31 (8), C(10), C(8 0 ), C(10 0 )), 123.04 (C(6) and C(6 0 )), 128.98 (C(3) and C(3 0 )), 132.09 (C(7), C(11), C(7 0 ), C(11 0 )), 136.10 (C(5) and C(5 0 )), 150.13 (C (9) and C(9 0 )), 186.63 (C(O)). 31 3 J CP ¼ 16.1 Hz), 54.36 (N(CH 2 ) 2 cyclic), 56.44 (NCH 2 CH 2 CH 2 CH 2 P), 61.21 (d, POCH 2 CH 3 , 2 J CP ¼ 6.2 Hz), 123.60 (C(8), C(10), C(8 0 ), C(10 0 )), 130.62 (C(7), C(11), C(7 0 ), C(11 0 )), 133.79 (C(5) and C(5 0 )), 135.63 (C(3) and C(3 0 )), 141.08 (C(6) and C(6 0 )), 147.31 (C(9) and C(9 0 )), 186.19 (C(O)). 31 To a stirred solution of the corresponding diethyl phosphonate (2 mmol) 7 dissolved in dry CHCl 3 (10 mL) a solution of bromotrimethylsilane (8 mmol) in dry CHCl 3 (3 mL) was added at one portion from syringe at room temperature.…”