Synthesis of bis(1,5-disubstituted tetrazoles) via double four component Azido-Ugi reaction

被引：2

作者：

Dehghan, Negin ^{[1
]}

Nasr-Isfahani, Hossein ^{[1
]}

Sarvary, Afshin ^{[2
]}

Bakherad, Mohammad ^{[1
]}

机构：

[1] Shahrood Univ Technol, Sch Chem, Shahrood 3619995161, Iran

[2] Babol Noshirvani Univ Technol, Dept Chem, Fac Sci, Shariati Ave, Babol 4714871167, Iran

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2021年 / 58卷 / 01期

关键词：

EFFICIENT SYNTHESIS; 1,5-DISUBSTITUTED TETRAZOLES; MULTICOMPONENT REACTIONS; DERIVATIVES; ISOCYANIDE; 3-COMPONENT; ACCESS;

D O I：

10.1002/jhet.4178

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A double four component Azido-Ugi reaction of isocyanide, TMSN3, aldehyde, and 4,4 '-sulfonyldianiline with two amine functional groups in MeOH at 65 degrees C has been described. The synthesis of pharmacologically and structurally interesting compounds with two 1,5-disubstituted tetrazole rings via a reaction from available and inexpensive reagents under a convenient process and mild reaction conditions has been reported. Modifications in the structure of the reaction product could be followed by varying the aldehyde or isocyanide component. The products are new and were well described by Mass, H-1 NMR, and C-13 NMR spectral studies.

引用

页码：350 / 356

页数：7

共 32 条

[1] Materials Functionalization with Multicomponent Reactions: State of the Art [J].

Afshari, Ronak ;

Shaabani, Ahmad .

ACS COMBINATORIAL SCIENCE, 2018, 20 (09) :499-528

[2] Synthesis of 1,5-disubstituted tetrazole-1,2,3 triazoles hybrids via Ugi-azide/CuAAC [J].

Aguilar-Morales, Cesia M. ;

de Loera, Denisse ;

Contreras-Celedon, Claudia ;

Cortes-Garcia, Carlos J. ;

Chacon-Garcia, Luis .

SYNTHETIC COMMUNICATIONS, 2019, 49 (16) :2086-2095

[3] Squaric acid is a suitable building-block in 4C-Ugi reaction: access to original bivalent compounds [J].

Aknin, Karen ;

Gauriot, Marion ;

Totobenazara, Jane ;

Deguine, Noemie ;

Deprez-Poulain, Rebecca ;

Deprez, Benoit ;

Charton, Julie .

TETRAHEDRON LETTERS, 2012, 53 (04) :458-461

[4] Efficient Synthesis of Novel Coumarin-3-carboxamides (=2-Oxo-2H-1-benzopyran-3-carboxamides) Containing Lipophilic Spacers [J].

Balalaie, Saeed ;

Bigdeli, Mohammad Ali ;

Sheikhhosseini, Enayatollah ;

Habibi, Azizollah ;

Moghadam, Hamed Piri ;

Naderi, Mehrnoush .

HELVETICA CHIMICA ACTA, 2012, 95 (03) :528-535

[5] Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles [J].

Barreto, Angelica de Fatima S. ;

dos Santos, Veronica Alves ;

Andrade, Carlos Kleber Z. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 :2596-2602

[6] Copper(I) catalyzed oxidative hydrolysis of Ugi 3-component and Ugi-azide reaction products towards 2° α-ketoamides and α-ketotetrazoles [J].

Collet, Jurrien W. ;

Foley, Christopher ;

Shaw, Arthur Y. ;

Orru, Romano V. A. ;

Ruijter, Eelco ;

Hulme, Christopher .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (29) :6132-6135

[7] Trimesic acid is a suitable building block in triple four-component Ugi reaction: access to unique trivalent compounds [J].

Dehghan, Negin ;

Nasr-Isfahani, Hossein ;

Sarvary, Afshin ;

Bakherad, Mohammad .

MONATSHEFTE FUR CHEMIE, 2020, 151 (03) :397-404

[8] Chemistry and Biology Of Multicomponent Reactions [J].

Domling, Alexander ;

Wang, Wei ;

Wang, Kan .

CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135

[9] A bidirectional access to novel thiadiazine hybrid molecules by double multicomponent reactions [J].

Echemendia, Radell ;

Rabelo, Waleria F. ;

Lopez, Ernesto R. ;

Coro, Julieta ;

Suarez, Margarita ;

Paixao, Marcio Weber ;

Rivera, Daniel G. .

TETRAHEDRON LETTERS, 2018, 59 (45) :4050-4053

[10]

Ghandi M., 2015, J HETEROCYCL CHEM, V54, P102

← 1 2 3 4 →