Synthesis of 5-oxo-1-substituted tetrazoles derived from amino acids

被引：0

作者：

Nagendra, G. ^{[1
]}

Narendra, N. ^{[2
]}

Sureshbabu, Vommina V. ^{[1
]}

机构：

[1] Bangalore Univ, Peptide Res Lab, Dept Studies Chem, Bangalore 560001, Karnataka, India

[2] Tumkur Univ, Dept Chem, Tumkur 570102, India

来源：

INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY | 2012年 / 51卷 / 03期

关键词：

Tetrazole; tetrazolone; isocyanate; oxazolidinone; cycloaddition; SOLID-PHASE SYNTHESIS; THERMAL REARRANGEMENT; IONIC LIQUIDS; POTENT; PHOTOCHEMISTRY; INHIBITORS; ALLYLOXYTETRAZOLES; ISOCYANATES; MOLECULES; CHEMISTRY;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein is described an application of amino acid derived isocyanates in the synthesis of 5-oxo-tetrazoles. A series of 1-substituted tetrazol-5-ones have been synthesized by [3+2] cycloaddition of N-Fmoc/Boc/Cbz protected beta-amino acid derived isocyanates and TMS-N-3. The protocol has also been extended for the insertion of oxo-tetrazolone moiety in the side chains of the Asp/Glu by employing oxazolidinone bidentate protection for C-alpha and N-alpha groups.

引用

页码：486 / 492

页数：7

共 56 条

[1] Synthesis of a cis-conformationally restricted peptide bond isostere and its application to the inhibition of the HIV-1 protease [J].

Abell, AD ;

Foulds, GJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (17) :2475-2482

[2] Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions [J].

Angell, Yu L. ;

Burgess, Kevin .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1674-1689

[3] Heteroaromatic benzyl ethers as intermediates for palladium-catalysed transfer hydrogenolysis of benzyl alcohols [J].

Araújo, NCP ;

Brigas, AF ;

Cristiano, MLS ;

Frija, LMT ;

Guimaraes, EMO ;

Loureiro, RMS .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 215 (1-2) :113-120

[4] Structural effects on sigmatropic shifts in heteroaromatic allyl ethers [J].

Araújo, NCP ;

Barroca, PMM ;

Bickley, JF ;

Brigas, AF ;

Cristiano, MLS ;

Johnstone, RAW ;

Loureiro, RMS ;

Pena, PCA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (09) :1213-1219

[5] DNA-binding of drugs used in medicinal therapies [J].

Bischoff, G ;

Hoffmann, S .

CURRENT MEDICINAL CHEMISTRY, 2002, 9 (03) :321-348

[6] Low temperature matrix-isolation and solid state vibrational spectra of tetrazole [J].

Bugalho, SCS ;

Maçôas, EMS ;

Cristiano, MLS ;

Fausto, R .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2001, 3 (17) :3541-3547

[7] A GENERAL AND EXPEDIENT METHOD FOR THE SOLID-PHASE SYNTHESIS OF 1,4-BENZODIAZEPINE DERIVATIVES [J].

BUNIN, BA ;

ELLMAN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10997-10998

[8] NEW EFFICIENT STRATEGY FOR THE INCORPORATION OF (S)-ISOSERINE INTO PEPTIDES [J].

BURGER, K ;

WINDEISEN, E ;

PIRES, R .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7641-7645

[9] The role of natural product chemistry in drug discovery [J].

Butler, MS .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (12) :2141-2153

[10] Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist [J].

Chung, JYL ;

Ho, GJ ;

Chartrain, M ;

Roberge, C ;

Zhao, DL ;

Leazer, J ;

Farr, R ;

Robbins, M ;

Emerson, K ;

Mathre, DJ ;

McNamara, JM ;

Hughes, DL ;

Grabowski, EJJ ;

Reider, PJ .

TETRAHEDRON LETTERS, 1999, 40 (37) :6739-6743

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