Inverse-electron-demand [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with 1,3,5-triazinanes: access to perfluoroalkylated tetrahydroquinazolines

被引：39

作者：

Liang, Dong ^{[1
]}

Tan, Li-Ping ^{[1
]}

Xiao, Wen-Jing ^{[1
,2
]}

Chen, Jia-Rong ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, CCNU uOttawa Joint Res Ctr,Key Lab Pesticide & Ch, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 26期

关键词：

METAL-FREE; SALTS; HEXAHYDRO-1,3,5-TRIAZINES;

D O I：

10.1039/d0cc00747a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with formaldimines is described for the synthesis of perfluoroalkylated tetrahydroquinazolines. Key to this process is the photocatalytic radical-mediated generation of aza-o-QMs from 2-vinylanilines and perfluoroalkyl radical precursors as well as the in situ release of formaldimines from 1,3,5-triazinanes.

引用

页码：3777 / 3780

页数：4

共 46 条

[1] Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].

Charpentier, Julie ;

Frueh, Natalja ;

Togni, Antonio .

CHEMICAL REVIEWS, 2015, 115 (02) :650-682

[2] Transition-Metal Free Construction of Isoquinoline-fused Triazines Containing Alkenyl C-X Bonds [J].

Cheng, Xiao ;

Cao, Xia ;

Zhou, Shuang-Jing ;

Cai, Bao-Gui ;

He, Xiang-Kui ;

Xuan, Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) :1230-1235

[3] Direct, efficient, solvent-free synthesis of 2-aryl-1,2,3,4-tetrahydroquinazolines [J].

Correa, WH ;

Papadopoulos, S ;

Radnidge, P ;

Roberts, BA ;

Scott, JL .

GREEN CHEMISTRY, 2002, 4 (03) :245-251

[4] Neuroprotective Tri- and Tetracyclic BChE Inhibitors Releasing Reversible Inhibitors upon Carbamate Transfer [J].

Darras, Fouad H. ;

Kling, Beata ;

Heilmann, Joerg ;

Decker, Michael .

ACS MEDICINAL CHEMISTRY LETTERS, 2012, 3 (11) :914-919

[5] Synthesis of Quinazolines and Tetrahydroquinazolines: Copper-Catalyzed Tandem Reactions of 2-Bromobenzyl Bromides with Aldehydes and Aqueous Ammonia or Amines [J].

Fan, Xuesen ;

Li, Bin ;

Guo, Shenghai ;

Wang, Yuanyuan ;

Zhang, Xinying .

CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (03) :739-743

[6]

Gall E. L., 1999, SYNLETT, P1383

[7] Synthesis of 2-Unsubstituted Pyrrolidines and Piperidines from Donor-Acceptor Cyclopropanes and Cyclobutanes: 1,3,5-Triazinanes as Surrogates for Formylimines [J].

Garve, Lennart K. B. ;

Kreft, Alexander ;

Jones, Peter G. ;

Werz, Daniel B. .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (17) :9235-9242

[8] Rhodium(ii)-catalyzed annulation of N-sulfonyl-1,2,3-triazoles with 1,3,5-triazinanes to produce octahydro-1H-purine derivatives: a combined experimental and computational study [J].

Ge, Jiemin ;

Wu, Xueli ;

Bao, Xiaoguang .

CHEMICAL COMMUNICATIONS, 2019, 55 (43) :6090-6093

[9] SYNTHESIS OF 1,2,3,4-TETRAHYDROQUINAZOLINE DERIVATIVES AS POTENTIAL ALPHA-ADRENERGIC BLOCKING-AGENTS [J].

GRANADOS, R ;

ALVAREZ, M ;

VALLS, N ;

SALAS, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (05) :1271-1275

[10] SYNTHESIS AND INVITRO STUDY OF PLATELET ANTIAGGREGANT ACTIVITY OF 1,2,3,4-TETRAHYDROQUINAZOLINE DERIVATIVES [J].

GRAVIER, D ;

DUPIN, JP ;

CASADEBAIG, F ;

HOU, G ;

BOISSEAU, M ;

BERNARD, H .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1989, 24 (05) :531-535

← 1 2 3 4 5 →