Regioselective Synthesis of 1-Cyano-3-arylindolizines: Construction of Pyrroles via DDQ-Mediated Ring Closure of Cyclopropyl Pyridines

被引：3

作者：

Joshi, Dirgha Raj ^{[1
,2
]}

Kim, Ikyon ^{[1
,2
]}

机构：

[1] Yonsei Univ, Coll Pharm, 85 Songdogwahak Ro, Incheon 21983, South Korea

[2] Yonsei Univ, Yonsei Inst Pharmaceut Sci, 85 Songdogwahak Ro, Incheon 21983, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 17期

基金：

新加坡国家研究基金会;

关键词：

Indolizine; Cyclopropanation; Annulation; Domino reaction; Oxidative cyclization; DONOR-ACCEPTOR CYCLOPROPANES; INDOLIZINES; CYCLIZATION; CYCLOADDITION; REARRANGEMENT; DERIVATIVES; ARYLATION; EXPANSION; OXIDATION; IODINE;

D O I：

10.1002/adsc.202200590

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A modular approach to a wide range of 1-cyano-3-(hetero)arylindolizines through aldol-cyclopropanation-oxidative cycloisomerization is described where DDQ was utilized for the regioselective synthesis of the pyrrole units from cyclopropyl pyridines for the first time. A key to success is regioselective oxidation of benzylic position by DDQ, which enabled us to access to one regioisomer out of two possible ones. Homo-dimerization at the C2, C5, or C7 sites of indolizines in the presence of DDQ has been discovered for the first time as well.

引用

页码：3016 / 3022

页数：7

共 50 条

[31] Palladium-catalyzed ring-opening of cyclopropyl benzamides: synthesis of benzo[c]azepine-1-ones via C(sp3)-H functionalization
Ladd, Carolyn L.
Roman, Daniela Sustac
Charette, Andre B.
TETRAHEDRON, 2013, 69 (22) : 4479 - 4487
[32] Synthesis of trifluoromethylthiolated azacalix[1] arene[3]pyridines from the Cu(II)-mediated direct trifluoromethylthiolation reaction of arenes via reactive arylcopper(III) intermediates
Wang, Fei
Zhao, Liang
You, Jingsong
Wang, Mei-Xiang
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (07): : 880 - 886
[33] Cu(OAc)2-Et3N mediated oxidative coupling of α-azido ketones with pyridinium ylides: utilizing in situ generated imines for regioselective synthesis ofimidazo[1,2-a]pyridines
Kamal, Ahmed
Reddy, Chada Narsimha
Satyaveni, Malasala
Chandrasekhar, D.
Nanubolu, Jagadeesh Babu
Singarapu, Kiran Kumar
Maurya, Ram Awatar
CHEMICAL COMMUNICATIONS, 2015, 51 (52) : 10475 - 10478
[34] ELECTRON-DEFICIENT 3-CYANO-1-(PARA-TOLUENESULFONYL)-1,3-BUTADIENES - REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF A BENZENE-RING SYSTEM BY MICHAEL-TYPE ADDITION-CYCLIZATION WITH ENAMINES
MASUYAMA, Y
YAMAZAKI, H
TOYODA, Y
KURUSU, Y
SYNTHESIS-STUTTGART, 1985, (10): : 964 - 966
[35] Metal-free synthesis of imidazo[1,5-a]pyridines via elemental sulfur mediated sequential dual oxidative Csp3-H amination
Sheng, Jie
Liu, Jidan
Zhao, He
Zheng, Liyao
Wei, Xingchuan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (31) : 5570 - 5574
[36] STEREOCOMPLEMENTARY CONSTRUCTION OF 2-ETHYNYL-3-HYDROXYTETRAHYDROFURAN DERIVATIVES VIA ENDO-MODE RING CLOSURE OF 3,4-EPOXY-6-SUBSTITUTEDHEX-5-YN-1-OLS
MUKAI, C
SUGIMOTO, Y
IKEDA, Y
HANAOKA, M
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (10) : 1161 - 1162
[37] Asymmetric synthesis of 3-substituted dihydro-2H-isoquinolin-1-ones, dihydro- and tetrahydroisoquinolines via 1,2-addition/ring closure
Enders, D
Braig, V
Boudou, M
Raabe, G
SYNTHESIS-STUTTGART, 2004, (18): : 2980 - 2990
[38] METAL-FREE REGIOSELECTIVE SYNTHESIS OF 2-NITRO-3-ARYLIMIDAZO[1,2-a]PYRIDINES VIA OXIDATIVE AMINATION UNDER AIR USING SILICA SULFURIC ACID AS AN EFFECTIVE HETEROGENEOUS CATALYST
Uppalapati, Divya Sree
Dachuru, Rama Sekhara Reddy
Sunkara, Satya Veni
HETEROCYCLES, 2021, 102 (07) : 1402 - 1411
[39] Synthesis of 1H-pyrazolo[3,4-d]pyrimidines via solid-phase Aza-Wittig/electrocyclic ring closure reaction
Liao, Subo
Xing, Li
Hamper, Bruce
TETRAHEDRON LETTERS, 2013, 54 (50) : 6855 - 6857
[40] An enolate-mediated regioselective synthesis of 1,2,3-triazoles via azide-aldehydes or ketones [3+2]-cycloaddition reactions in aqueous phase
Tripathi, Anupam
Rode, Chandrashekhar, V
Llop, Jordi
Chavan, Subhash P.
Joshi, Sameer M.
TETRAHEDRON LETTERS, 2020, 61 (13)

← 1 2 3 4 5 →