1-Alkyl-5-((di)alkylamino) Tetrazoles: Building Blocks for Peptide Surrogates

被引：8

作者：

Tymtsunik, Andriy V. ^{[1
,2
]}

Bilenko, Vitaliy A. ^{[2
]}

Kokhan, Serhiy O. ^{[1
,2
]}

Grygorenko, Oleksandr O. ^{[1
,2
]}

Volochnyuk, Dmitriy M. ^{[2
]}

Komarov, Igor V. ^{[1
,2
]}

机构：

[1] Kyiv Natl Taras Shevchenko Univ, UA-01601 Kiev, Ukraine

[2] Enamine Ltd, UA-01103 Kiev, Ukraine

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 02期

关键词：

CIS-AMIDE BOND; ACID; INHIBITORS; CHEMISTRY; DISCOVERY; ANALOGS; ISOSTERES; DESIGN; ANIONS;

D O I：

10.1021/jo2022235

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach to the synthesis of 1-alkyl-5-((di)allcylamino)tetrazoles by nucleophilic substitution in 1-alkyl-5-sulfonyl-tetrazoles with anions generated from the primary secondary amines was developed. Tolerance of the method to the presence of some functional groups (i.e., protected amine) in both components of the reaction was demonstrated. Obtained tetrazoles are promising building blocks for the design of peptide surrogates, in particular, for replacement approaches of alkyl urea derivatives.

引用

页码：1174 / 1180

页数：7

共 50 条

[41] 5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks
Danilkina, Natalia A.
Govdi, Anastasia, I
Balova, Irina A.
SYNTHESIS-STUTTGART, 2020, 52 (13): : 1874 - 1896
[42] ELECTRON EFFECTS IN 1-(P-METHOXYPHENYL)-5-[4-ALKYL-1-(P-METHOXYPHENYL)-4,5-DIHYDROTETRAZOLYL-5-CHLOROMETHYLENE]TETRAZOLES
ROZHENKO, AB
PIROZHENKO, VV
DASHKOVSKAYA, EV
SHIVANYUK, AF
LOZINSKAYA, MO
ZHURNAL ORGANICHESKOI KHIMII, 1993, 29 (02): : 246 - 253
[43] Building blocks for the solution phase synthesis of oligonucleotides:: Regioselective hydrolysis of 3′,5′-Di-O-levulinylnucleosides using an enzymatic approach
García, J
Fernández, S
Ferrero, M
Sanghvi, YS
Gotor, V
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13): : 4513 - 4519
[44] An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles
Agafonova, Anastasiya, V
Funt, Liya D.
Novikov, Mikhail S.
Khlebnikov, Alexander F.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (09) : 1976 - 1984
[45] Di(1H-tetrazol-5-yl) methanone oxime and 5,5′-(hydrazonomethylene) bis(1H-tetrazole) and their salts: a family of highly useful new tetrazoles and energetic materials
Chand, Deepak
Parrish, Damon A.
Shreeve, Jean'ne M.
JOURNAL OF MATERIALS CHEMISTRY A, 2013, 1 (48) : 15383 - 15389
[46] β-Nitroacrylates as key building blocks for the synthesis of alkyl 3-substituted 5-oxopiperazine-2-carboxylates under fully heterogeneous conditions
Serena Gabrielli
Roberto Ballini
Alessandro Palmieri
Monatshefte für Chemie - Chemical Monthly, 2013, 144 : 509 - 514
[47] β-Nitroacrylates as key building blocks for the synthesis of alkyl 3-substituted 5-oxopiperazine-2-carboxylates under fully heterogeneous conditions
Gabrielli, Serena
Ballini, Roberto
Palmieri, Alessandro
MONATSHEFTE FUR CHEMIE, 2013, 144 (04): : 509 - 514
[48] 1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles
Aguilar, Enrique
Sanz, Roberto
Fernandez-Rodriguez, Manuel A.
Garcia-Garcia, Patricia
CHEMICAL REVIEWS, 2016, 116 (14) : 8256 - 8311
[49] 1,2,5,6-Naphthalene Diimides: A Class of Promising Building Blocks for Organic Semiconductors
Zhao, Zheng
Ge, Congwu
Zhao, Xueqian
Huang, Jintao
Gao, Xike
CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (10): : 1226 - 1234
[50] Synthesis of 1,2,5,6-and 1,4,5,8-anthracenetetrone: Building blocks for -conjugated small molecules and polymers
Gloecklhofer, Florian
Stoeger, Berthold
Froehlich, Johannes
SYNTHETIC COMMUNICATIONS, 2018, 48 (18) : 2358 - 2365

← 1 2 3 4 5 →