Boron Trifluoride-Mediated Cycloaddition of 3-Bromotetrazine and Silyl Enol Ethers: Synthesis of 3-Bromo-pyridazines

被引：11

作者：

Schnell, Simon D. ^{[1
]}

Gonzalez, Jorge A. ^{[1
]}

Sklyaruk, Jan ^{[1
]}

Linden, Anthony ^{[1
]}

Gademann, Karl ^{[1
]}

机构：

[1] Univ Zurich, Dept Chem, CH-8057 Zurich, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 17期

关键词：

DIELS-ALDER REACTIONS; CROSS-COUPLING REACTIONS; FUNCTIONALIZATION; 1,2-DIAZINE; TETRAZINES; ACTIVATION; INHIBITORS; PYRROLES; NITROGEN; SYSTEM;

D O I：

10.1021/acs.joc.1c01384

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyridazines are important scaffolds for medicinal chemistry or crop protection agents, yet the selective preparation of 3-bromo-pyridazines with high regiocontrol remains difficult. We achieved the Lewis acid-mediated inverse electron demand Diels-Alder reaction between 3-monosubstituted s-tetrazine and silyl enol ethers and obtained functionalized pyridazines. In the case of 1-monosubstituted silyl enol ethers, exclusive regioselectivity was observed. Downstream functionalization of the resulting 3-bromo-pyridazines was demonstrated utilizing several cross-coupling protocols to synthesize 3,4-disubstituted pyridazines with excellent control over the substitution pattern.

引用

页码：12008 / 12023

页数：16

共 50 条

[1] Formal (3+3) Cycloaddition of Silyl Enol Ethers Catalyzed by Trifric Imide: Domino Michael Addition-Claisen Condensation Accompanied with Isomerization of Silyl Enol Ethers
Azuma, Takumi
Takemoto, Yoshiji
Takasu, Kiyosei
CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59 (09) : 1190 - 1193
[2] Formal [4+2] cycloaddition between 3-ethoxycyclobutanones and silyl enol ethers
Matsuo, Jun-ichi
Negishi, Shoko
Ishibashi, Hiroyuki
TETRAHEDRON LETTERS, 2009, 50 (42) : 5831 - 5833
[3] [4+3] CYCLOADDITION REACTION OF SOME SILYL ENOL ETHERS HAVING A CONJUGATED CARBONYL FUNCTIONALITY
OHNO, M
MORI, K
HATTORI, T
EGUCHI, S
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25): : 6086 - 6091
[4] DIASTEREOSELECTIVE [3+2] CYCLOADDITION OF METHYL 2-PHENLTHIOCYCLOPROPYL KETONE WITH ENOL SILYL ETHERS - SYNTHESIS OF FUNCTIONALIZED CYCLOPENTANES
HORIGUCHI, Y
SUEHIRO, I
SASAKI, A
KUWAJIMA, I
TETRAHEDRON LETTERS, 1993, 34 (38) : 6077 - 6080
[5] Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers
Scherbinina, Sofya I.
Fedorov, Oleg V.
Levin, Vitalij V.
Kokorekin, Vladimir A.
Struchkova, Marina I.
Dilman, Alexander D.
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24): : 12967 - 12974
[6] Catalytic Asymmetric [3+2] Cycloaddition of Exocyclic Enol Ethers for the Synthesis of Spiroketals
Zhang, Fengcai
Zhou, Yuqiao
Zhao, Hansen
Chen, Long
Cao, Weidi
Feng, Xiaoming
PRECISION CHEMISTRY, 2023, 1 (07): : 423 - 428
[7] Synthesis of diaryl ethers based on one-pot [3+3] cyclizations of 1,3-bis(silyl enol ethers)
Sher, Muhammad
Ahmed, Zafar
Rashid, Muhammad A.
Fischer, Christine
Spannenberg, Anke
Langer, Peter
TETRAHEDRON, 2007, 63 (23) : 4929 - 4936
[8] SYNTHESIS OF CYCLOPENT-2-ENONES THROUGH STEPWISE [3+2] CYCLOADDITION OF SIMPLE SILYL ENOL ETHERS AND ALK-1-YNES
YAMAGUCHI, M
SEHATA, M
HAYASHI, A
HIRAMA, M
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (22) : 1708 - 1709
[9] Stereoselective synthesis of thioxanthone derivatives from 3-(trifluoroacetyl)thiochromone and bis(silyl enol ethers)
V. O. Iaroshenko
A. Bunescu
D. V. Sevenard
V. Ya. Sosnovskikh
P. Langer
Russian Chemical Bulletin, 2015, 64 : 470 - 472
[10] Boron trifluoride mediated synthesis of 3-methyl-1,2-dihydronapthalenes.
Kabalka, GW
Malladi, RR
Li, NS
Tejedor, D
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U164 - U165

← 1 2 3 4 5 →