Simple, Efficient, and Catalyst-Free Synthesis of (2-Amino-4H-1-benzopyran-4-yl)phosphonates in Polyethylene Glycol

被引：28

作者：

Das, Biswanath ^{[1
]}

Balasubramanyam, Penagaluri ^{[1
]}

Reddy, Gandollo Chinna ^{[1
]}

Salvanna, Nayaki ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

HELVETICA CHIMICA ACTA | 2011年 / 94卷 / 07期

关键词：

STATE ANALOG INHIBITORS; ONE-POT SYNTHESIS; ACID; DERIVATIVES;

D O I：

10.1002/hlca.201000461

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Several (2-amino-4H-1-benzopyran-4-yl)phosphonates were efficiently synthesized by employing a multicomponent protocol involving a salicylaldehyde, malononitrile or ethyl cyanoacetate, and a trialkyl phosphite in polyethylene glycol. The latter could be recovered and re-used. No additional solvent or catalyst was required. To the best of our knowledge, this is the first report of the one-pot preparation of (2-amino-4H-1-benzopyran-4-yl)phosphonic acid dimethyl esters.

引用

页码：1347 / 1350

页数：4

共 12 条

[1] RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].

ALLEN, MC ;

FUHRER, W ;

TUCK, B ;

WADE, R ;

WOOD, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661

[2] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID [J].

ATHERTON, FR ;

HASSALL, CH ;

LAMBERT, RW .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) :29-40

[3] Osmium tetroxide in poly(ethylene glycol) (PEG): a recyclable reaction medium for rapid asymmetric dihydroxylation under Sharpless conditions [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Sultana, SS ;

Reddy, NR .

CHEMICAL COMMUNICATIONS, 2003, (14) :1716-1717

[4] Simple and Efficient Access to N-Tosyl β-Amino Ketones and Their Conversion into 2,4-Disubstituted Azetidines [J].

Das, Biswanath ;

Balasubramanyam, Penagaluri ;

Veeranjaneyulu, Boyapati ;

Reddy, Gandolla Chinna .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) :9505-9508

[5] Synthesis of α-Aminonitriles through Strecker Reaction of N-Tosylaldimines Using Molecular Iodine [J].

Das, Biswanath ;

Balasubramanyam, Penagaluri ;

Krishnaiah, Maddeboina ;

Veeranjaneyulu, Boyapati ;

Reddy, Gandolla Chinna .

SYNTHESIS-STUTTGART, 2009, (20) :3467-3471

[6] Iodine-Catalyzed Efficient Hydrophosphonylation of N-Tosyl Aldimines [J].

Das, Biswanath ;

Balasubramanyam, Penagaluri ;

Krishnaiah, Maddeboina ;

Veeranjaneyulu, Boyapati ;

Reddy, Gandolla Chinna .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) :4393-4395

[7] Soluble polymers as scaffolds for recoverable catalysts and reagents [J].

Dickerson, TJ ;

Reed, NN ;

Janda, KD .

CHEMICAL REVIEWS, 2002, 102 (10) :3325-3343

[8]

Gaied L B, 2000, PHOSPHORUS SULFUR, V165, P17

[9] Indium Trichloride Catalyzed One-Pot Synthesis of New (2-Amino-3-cyano-4H-chromen-4-yl) Phosphonic Acid Diethyl Ester [J].

Jayashree, Parthasarathy ;

Shanthi, Gnanamani ;

Perumal, Paramasivan T. .

SYNLETT, 2009, (06) :917-920

[10] BIOLOGICAL-ACTIVITY OF AMINOPHOSPHONIC ACIDS [J].

KAFARSKI, P ;

LEJCZAK, B .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 63 (1-2) :193-215

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