One-Pot Synthesis of Polysubstituted 3-Amino-2-oxo-2,7-dihydro-1H-azepines

被引：1

作者：

Liao, Shengrong ^{[1
]}

Qin, Chun ^{[1
]}

Yao, Peifen ^{[2
]}

Li, Jinsheng ^{[1
]}

Zhou, Xuefeng ^{[1
]}

Wang, Junfeng ^{[1
]}

Huang, Zhishu ^{[2
]}

Liu, Yonghong ^{[1
]}

机构：

[1] Chinese Acad Sci, South China Sea Inst Oceanol,Ctr Marine Microbiol, CAS Key Lab Trop Marine Bioresources & Ecol, Guangdong Key Lab Marine Mat Med,RNAM, Guangzhou 510301, Guangdong, Peoples R China

[2] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2014年 / 46卷 / 05期

基金：

中国国家自然科学基金;

关键词：

alkyne; 3-aminoazepan-2-one; Michael addition; piperazine-2,5-dione; protecting groups; MYCOBACTERIUM-TUBERCULOSIS; BECKMANN REARRANGEMENT; INHIBITORS; LACTAMS; DERIVATIVES; METATHESIS; ALKALOIDS; CHEMISTRY; DISCOVERY; ANALOGS;

D O I：

10.1055/s-0033-1340473

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient synthesis of novel seven-membered heterocyclic derivatives containing 3-aminoazepan-2-one backbone is described using 1,4-protected piperazine-2,5-diones and alkynes as starting materials. The reaction may undergo Michael addition, unusual nucleophilic attack to an amide group, and keto-enol tautomerization. The reaction showed different reactivity when using substrates with different protecting groups: it had higher efficiency when using either alkanoyl-protecting group with cesium carbonate as the base, or benzoyl-protecting group with triethylamine as the base, but no reaction when using benzyl or allyl protecting groups with a variety of bases (Et3N, DBU, K2CO3, Cs2CO3, KHCO3, CsHCO3, and KOt-Bu).

引用

页码：621 / 628

页数：8

共 50 条

[31] One-pot synthesis of 4-amino-1,2-dihydro-3-quinolinecarboxylic acid derivatives
Kobayashi, K
Takabatake, H
Kitamura, T
Morikawa, O
Konishi, H
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (07) : 1697 - 1699
[32] One-pot synthesis of bis (phenylimino dihydro thiazolyl-2H-chromene) derivatives
Pavurala, Sreenu
Vaarla, Krishnaiah
Vedula, Rajeswar Rao
SYNTHETIC COMMUNICATIONS, 2017, 47 (04) : 330 - 334
[33] One-Pot N -α-C(sp3 )- H Bond Functionalisation Cascade for the Synthesis of Polysubstituted Imidazoles
Kadu, Vikas D.
Sankala, Naga Chandradudu
Hublikar, Mahesh G.
Bansode, Shahaji I.
Bhosale, Raghunath B.
SYNTHESIS-STUTTGART, 2024, 56 (14): : 2277 - 2283
[34] Highly efficient one-pot synthesis of 1,2-dihydro-2-oxo-3-pyridinecarboxylate derivatives by FeCl3-promoted [3+3] annulation
Wang, SZ
Tan, T
Li, JX
Hu, HW
SYNLETT, 2005, (17) : 2658 - 2660
[35] One-Pot Synthesis of 2-Amino-indole-3-carboxamide and Analogous
Wang, Kan
Herdtweck, Eberhardt
Doemling, Alexander
ACS COMBINATORIAL SCIENCE, 2011, 13 (02) : 140 - 146
[36] One-pot synthesis of substituted 3-amino-2-nitrothiophenes and selenophenes
Thomae, David
Dominguez, Juan Carlos Rodriguez
Kirsch, Gilbert
Seek, Pierre
TETRAHEDRON, 2008, 64 (14) : 3232 - 3235
[37] Unsaturated carboxylic acids in the one-pot synthesis of novel derivatives of 3,4-dihydro-2H-thiopyran
Merkulova, Ekaterina A.
Kolobov, Aleksei V.
Ovchinnikov, Konstantin L.
Khrustalev, Victor N.
Nenajdenko, Valentine G.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (03) : 245 - 252
[38] Unsaturated carboxylic acids in the one-pot synthesis of novel derivatives of 3,4-dihydro-2H-thiopyran
Ekaterina А. Merkulova
Aleksei V. Kolobov
Konstantin L. Ovchinnikov
Victor N. Khrustalev
Valentine G. Nenajdenko
Chemistry of Heterocyclic Compounds, 2021, 57 : 245 - 252
[39] ONE-POT SYNTHESIS OF OCTAHYDRO-2-CYCLIC-AMINO-1H-1,3,2-BENZODIAZAPHOSPHOLE 2-OXIDES
REDDY, CD
RAO, CVN
AMMANNI, H
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1989, 28 (01): : 62 - 63
[40] One-Pot Synthesis of Fluorescent 3-Amino-2-arylquinolin-4(1 H )-ones from Isatoic Anhydride and 1-(2-Oxo-2-arylethyl)pyridinium Salts
Kirnosov, Sergey A.
Shatsauskas, Anton L.
Petrova, Alina, V
Zheleznova, Tatyana Y. U.
Shuvalov, Vladislav Y. U.
Kostyuchenko, Anastasia S.
Fisyuk, Alexander S.
SYNTHESIS-STUTTGART, 2025,

← 1 2 3 4 5 →