H14[NaP5W30O110] as an Efficient Catalyst for the One-Pot Synthesis of α-Amino Nitriles

Hossein A. Oskooie; Majid M. Heravi; Khadijeh Bakhtiari; Vahideh Zadsirjan; Fatemeh F. Bamoharram

doi:10.1055/s-2006-944206

LETTER

H₁₄[NaP₅W₃₀O₁₁₀] as an Efficient Catalyst for the One-Pot Synthesis of α-Amino Nitriles

Hossein A. Oskooie^a, Majid M. Heravi*^a, Khadijeh Bakhtiari^a, Vahideh Zadsirjan^a, Fatemeh F. Bamoharram^b
^a Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iran
e-Mail: mmh1331@yahoo.com;
^b Department of Chemistry, School of Sciences, Azad University, Mashhad, Iran

Abstract

All articles of this category

Abstract

In this study, the synthesis of some α-amino nitriles is reported. The compounds were prepared by the nucleophilic addition reaction of aldehydes and amines with TMSCN in the presence of a catalytic amount of H₁₄[NaP₅W₃₀O₁₁₀], Preyssler’s heteropoly acid, in excellent yields. The catalyst can be recovered and reused in subsequent reactions.

Key words

α-amino nitriles - heteropoly acids - TMSCN - trimethylsilyl cyanide

Full Text

References

<A NAME="RD03606ST-1">1</A> Dyker G. Angew. Chem., Int. Ed. Engl. 1997, 36: 1700

<A NAME="RD03606ST-2A">2a</A> Weinstock LM. Davis P. Handelsman B. Tull R. J. Org. Chem. 1967, 32: 2823

<A NAME="RD03606ST-2B">2b</A> Matier WL. Owens DA. Comer WT. Deitchman D. Ferguson HC. Seidehamel RJ. Young JR. J. Med. Chem. 1973, 16: 901

<A NAME="RD03606ST-3">3</A> Mai K. Patil G. Tetrahedron Lett. 1984, 25: 4583

<A NAME="RD03606ST-4">4</A> Groger H. Chem. Rev. 2003, 103: 2795

<A NAME="RD03606ST-5">5</A> Iyer MS. Gigstad M. Namdev ND. Lipton M. J. Am. Chem. Soc. 1996, 118: 4910

<A NAME="RD03606ST-6">6</A> Sigman MS. Jacobsen EN. J. Am. Chem. Soc. 1998, 120: 5315

<A NAME="RD03606ST-7">7</A> Ranu BC. Dey SS. Hajra A. Tetrahedron 2002, 58: 2529

<A NAME="RD03606ST-8">8</A> Yadav JS. Subba Reddy BV. Eeshwaraiah B. Srinivas M. Tetrahedron 2004, 60: 1767

<A NAME="RD03606ST-9">9</A> De SK. Gibbs RA. Tetrahedron Lett. 2004, 45: 7407

<A NAME="RD03606ST-10">10</A> De SK. Synth. Commun. 2005, 35: 1577

<A NAME="RD03606ST-11">11</A> De SK. J. Mol. Catal. A: Chem. 2005, 225: 169

<A NAME="RD03606ST-12">12</A> Yadav JS. Reddy BVS. Eshwaraiah B. Srinivas M. Vishnumurthy P. New. J. Chem. 2003, 27: 462

<A NAME="RD03606ST-13">13</A> Royer L. De SK. Gibbs RA. Terahedron Lett. 2005, 46: 4595

<A NAME="RD03606ST-14">14</A> Heydari A. Fatemi P. Alizadeh AA. Tetrahedron Lett. 1998, 39: 3049

<A NAME="RD03606ST-15">15</A> Strecker A. Ann. Chem. Pharm. 1850, 75: 27

<A NAME="RD03606ST-16">16</A> Harusawa S. Hamada Y. Shioiri T. Tetrahedron Lett. 1979, 20: 4663

<A NAME="RD03606ST-17A">17a</A> Chakraborty TK. Readdy GV. Hussain KA. Tetrahedron Lett. 1991, 32: 7597

<A NAME="RD03606ST-17B">17b</A> Leblanc JP. Gibson HW. Tetrahedron Lett. 1992, 33: 6295

<A NAME="RD03606ST-18A">18a</A> Kozhevnikov IV. Chem. Rev. 1998, 98: 171

<A NAME="RD03606ST-18B">18b</A> Kozhevnikov IV. Catal. Rev. Sci. Eng. 1995, 37: 311

<A NAME="RD03606ST-18C">18c</A> Okuhara T. Mizuno N. Misono M. Adv. Catal. 1996, 41: 113

<A NAME="RD03606ST-19A">19a</A> Ono Y. Perspectives in Catalysis Thomas JM. Zamaraev KI. Blackwell; London: 1992. p.431

<A NAME="RD03606ST-19B">19b</A> Misono M. Stud. Surf. Sci. Catal. 1993, 75: 69

<A NAME="RD03606ST-19C">19c</A> Izumi Y. Urabe K. Onaka M. Zeolite Clay and Heteropoly Acid in Organic Reactions Kodansha/VCH; Tokyo/New York: 1993. Chap. 3.

<A NAME="RD03606ST-20">20</A> Heravi MM. Derikvand F. Bamoharram FF. J. Mol. Catal. A: Chem. 2005, 242: 173

<A NAME="RD03606ST-21A">21a</A> Heravi MM. Ajami D. Ghassemzadeh M. Synthesis 1999, 339

<A NAME="RD03606ST-21B">21b</A> Heravi MM. Ajami D. Mojtahedi MM. Ghassemzadeh M. Tetrahedron Lett. 1999, 40: 561

<A NAME="RD03606ST-21C">21c</A> Heravi MM. Ajami D. Aghapoor K. Ghassemzadeh M. Chem. Commun. 1993, 833

<A NAME="RD03606ST-21D">21d</A> Heravi MM. Hekmat Shoar R. Pedram L. J. Mol. Catal. A: Chem. 2005, 231: 89

<A NAME="RD03606ST-22">22</A> Chen W.-Y. Lu J. Synlett 2005, 2293