One-pot synthesis of 2-phenylaminothiazolines from N-2-hydroxyethyl)-N′-phenylthioureas

Utility of Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas for Metal-Free Carbon–Phosphorus Bond Construction toward Regio- and Stereoselective Formation of Vinylphosphonates

“…2-Chloro-1,3-diphenyl-1,3,2-diazaphospholidine (1.00 g, 3.62 mmol), 1-(2-hydroxyethyl)-1-methyl-3-phenylthiourea (0.758 g, 3.62 mmol), and triethylamine (0.438 g, 4.34 mmol) in DCM (25 mL) were subjected to the reaction conditions described in GP-1 . Colorless solid 1o (0.460 g, 1.02 mmol, 29%).…”

“…35−4.29 (m, 1H), 3.92−3.68 (m, 4H), 3.52 (t, J = 4.9, Hz, 2H), 1.01 (d, t, J = 6.5 Hz, 3H); 13 C NMR (100.5 MHz, CDCl 3 ): δ 180.9, 144.8 (dd, J = 17.9, 3.7 Hz), 136.5,129.7,129.4 (d,J = 9.7 Hz),126.7,124.7,120.1,115.42 1-(2-((1,3-Diphenyl-1,3,2-diazaphospholidin-2-yl)oxy)ethyl)-1methyl-3-phenylthiourea (1o). 2-Chloro-1,3-diphenyl-1,3,2-diazaphospholidine 31 (1.00 g, 3.62 mmol), 1-(2-hydroxyethyl)-1-methyl-3phenylthiourea 42 (0.758 g, 3.62 mmol), and triethylamine (0.438 g, 4.34 mmol) in DCM (25 mL) were subjected to the reaction conditions described in GP-1. Colorless solid 1o (0.460 g, 1.02 mmol, 29%).…”

1,3,2-Diazaphospholidine (N-Heterocyclic Phosphine)-Mediated Carbon–Phosphorus Bond-Forming, One-Pot Tandem Reaction: A Route to α-Amino Phosphonates

“…2-Chloro-1,3-diphenyl-1,3,2-diazaphospholidine (1.00 g, 3.62 mmol), 1-(2-hydroxyethyl)-1-methyl-3-phenylthiourea (0.758 g, 3.62 mmol), and triethylamine (0.438 g, 4.34 mmol) in dry DCM (25 mL) were subjected to the reaction conditions described in GP-1 . Colorless solid 3d (0.460 g, 1.02 mmol, 29%).…”

“…mp: 112−113 °C. IR (KBr, cm −1 ): 3394, 3182, 3020, 2866, 1597, 1496, 1276, 4,129.0,127.4,120.3,115.4,115.2 (d,J = 9.7 Hz), 61.9, 55.5, 47.5 (d, J = 9.7 Hz), 45.9; 31 19 (1.00 g, 3.62 mmol), 1-(2-hydroxyethyl)-1-methyl-3phenylthiourea 23 (0.758 g, 3.62 mmol), and triethylamine (0.438 g, 4.34 mmol) in dry DCM (25 mL) were subjected to the reaction conditions described in GP-1. Colorless solid 3d (0.460 g, 1.02 mmol, 29%).…”

Thiourea and Selenourea and Their Applications

“…bromoketones, b=ketones (X=CO) or acrylic dienophiles (X=CH 2 ) Scheme 24.pyrimido[2,1-b][1,3]thiazines without any regioisomeric ambiguity (Scheme 24)[43,44].Whereas the use of 1,3-dicyclohexylcarbodiimide (DCC) affords 1,3-oxazolines from the N-(2-hydroxyethyl)thioureas (Scheme 25)[45][46][47]. 2-Phenylamino-1,3-thiazolines have been synthesized from N-(2-hydroxyethyl)-N'-alkylthioureas by a one-pot intramolecular Mitsunobu reaction.…”