[HP(HNCH₂CH₂)₃N]NO₃: An Efficient Homogeneous and Solid‐Supported Promoter for aza and thia‐Michael Reactions and for Strecker Reactions.

Abstract

FETTERLY, B. M.; JANA, N. K.; VERKADE*, J. G.; Tetrahedron 62 (2006) 2-3, p440-p456; Dep. Chem., Iowa State Univ., Ames, IA 50011, USA; Eng.) -Y. Steudel 22-033

Manganese (II) Chloride-Catalyzed Conjugated Addition of Amines to Electron Deficient Alkenes in Methanol-Water Medium~!2009-10-16~!2009-12-15~!2010-03-30~!

“…The reactions proceeded smoothly at room temperature and the products were obtained in excellent yields (entries 18-21). Several substituted anilines such as methyl, methoxy and flouro anilines underwent efficient additions with acrylonitrile and methyl acrylate giving only monoadducts in high yields under the present reaction conditions (entries [22][23][24][25]. Sensitive functional groups in aniline such as 3,4-(methylenedioxy)aniline also reacted well to give the desired product in good yields keeping the methylenedioxy group unaffected (entry 27).…”

“…Usually these conjugate additions are carried out in the presence of a strong base or acid [5]. To avoid this harsh conditions, a number of milder procedures have been developed over the past few years using a variety of reagents such as SnCl 4 /FeCl 3 [6], InCl 3 [7], CeCl 3 .7H 2 O-NaI [8], Yb(OTf) 3 [9], Cu(OTf) 2 [10], CAN [11], Bi(NO 3 ) 3 [12], Bi(OTf) 3 [13], LiClO 4 [14], KF/alumina [15], SmI 2 [16], Cu(acac) 2 /ionic liquid [17], ionic liquid/quaternary ammonium salt in water [18], boric acid in water [19],cyclodextrin [20], ZrOCl 2 .8H 2 O [21], borax [22], bromodimethylsulfonium bromide [23], [HP(HNCH 2 CH 2 ) 3 N]NO 3 [24], palladium [25] and nickel [26] etc. Although these methods are quite useful, many of these procedures require a large excess of reagents, long reaction time, drastic reaction conditions and toxic reagents as well as harmful solvents such as acetonitrile or 1,2-dichloroethane.…”

Synthesis and Characterization of New Complexes of 2-(6- Methoxybenzo[d]thiazol-2-ylamino)-2-phenyl acetonitrile Ligand with Manganese (II), Cobalt (II), Nickel (II), Copper (II), Zinc (II) Cadmium (II) and Mercury (II) Divalent Transition Metal Ions

“…Metal and elemental analysis of all compounds is represented in table (1) as well. The ligand 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-phenyl acetonitrile was prepared as reported in literature [17]. It was characterized by elemental analysis and infrared spectral data.…”

“…Moreover, among many other applications, they are readily hydrolyzed to diamines, which are of interest as ligands for Platinum (ІІ) complexes with potential antitumor properties [14,15]. Several modifications of the Strecker reaction have been reported using a variety of cyanating agent such as α-trimethylsiloxynitriles and under various reaction conditions [16,17]. Complexes with dinitrogen N2 ligand are of interest not only in theoretically but also from a practical point of view.…”

Development of epoxy nanofiltration membranes into smart materials for chemical separations

“…Numerous publications have reported on the aza-Michael addition of anilines to acrylates. [195][196][197][198][199] Diacrylates and diamines produce viable OSN membranes based on prior work in our lab, and this may prove to be an exciting alternative approach for synthesis of a light stimulus-responsive membrane. Overall the coating was found to be relatively uniform, less than 50 nm thick, and conformal to device microwires.…”