Divergent and Nucleophile-Assisted Rearrangement in the Construction of Pyrrolo[2,1-b][3]benzazepine and Pyrido[2,1-a]isoquinoline Scaffolds

被引：2

作者：

Obydennik, Arina Y. ^{[1
]}

Titov, Alexander A. ^{[1
]}

Listratova, Anna V. ^{[1
]}

Borisova, Tatiana N. ^{[1
]}

Sokolova, Irina L. ^{[1
]}

Rybakov, Victor B. ^{[2
]}

Van der Eycken, Erik V. ^{[1
,3
]}

Voskressensky, Leonid G. ^{[1
]}

Varlamov, Alexey V. ^{[1
]}

机构：

[1] RUDN Univ, Peoples Friendship Univ Russia, Sci Fac, Organ Chem Dept, 6 Miklukho Maklaya St, Moscow 117198, Russia

[2] Lomonosov Moscow State Univ, Dept Chem, Leninskie Gory 1-3, Moscow 119991, Russia

[3] Univ Leuven, Dept Chem, LOMAC, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2024年 / 30卷 / 03期

基金：

俄罗斯科学基金会;

关键词：

pyrrolo[2,1-b][3]benzazepines; pyrido[2,1-a]isoquinolines; pyrrolo[2,1-a]isoquinolines; microwave irradiation; sigmatropic rearrangement; SYSTEMS;

D O I：

10.1002/chem.202302919

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Under microwave (MW) irradiation at 150 degree celsius in toluene and in the presence of nucleophiles (DMAP, triphenylphosphine and tetrahydrothiophene) 1-substituted 1-ethynyl-2-vinyldi- and tetrahydroisoquinolines undergo [3,3]-sigmatropic rearrangement providing pyrrolo[2,1-b][3]benzazepines in good yields. The replacement of toluene with acetonitrile directs the rearrangement towards the formation of 7,11b-dihydro-6H-pyrido[2,1-a]isoquinolines.

引用

页数：6

共 50 条

[31] Nucleophile-induced ring contraction in pyrrolo[2,1-c][1,4]benzothiazines: access to pyrrolo[2,1-b][1,3]benzothiazoles
Lystsova, Ekaterina A.
V. Dmitriev, Maksim
Maslivets, Andrey N.
Khramtsova, Ekaterina E.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2023, 19 : 646 - 657
[32] Recent advances in the synthesis of chromenone fused pyrrolo[2,1-a]isoquinoline derivatives
Bera, Sonali
Maji, Avishek
Patra, Susanta
Mahanty, Dibyendu Sekhar
Samanta, Shubhankar
Samanta, Swarna Kamal
Biswas, Biplab
Patra, Prasanta
NEW JOURNAL OF CHEMISTRY, 2023, 47 (48) : 22246 - 22268
[33] Dimethyl 3-(cyclopropylcarbonyl)pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate
Xing, Honglong
Tang, Fan
Wang, Wei
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1430 - +
[34] NOVEL REARRANGEMENT OF 8H-ISOQUINO[2,1-B] [2]BENZAZOCINES TO "3-PHENYLPYRROLO[2,1-A]ISOQUINOLINES AND RELATED-COMPOUNDS
HANAOKA, M
WADA, A
SAKAMOTO, Y
ICHIHARA, M
YASUDA, S
IMANISHI, T
HETEROCYCLES, 1981, 16 (11) : 1933 - 1936
[35] Construction of Spiro[indene-2,1-pyrrolo[2,1-a]isoquinoline]s through a Visible-Light-Catalyzed Oxidative [3+2] Cycloaddition Reaction
Jiang, Yan-Hong
Sun, Jing
Sun, Qiu
Yan, Chao-Guo
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (07) : 862 - 866
[36] Diastereoselective construction of pyrrolo[2,1-a]isoquinoline-based bispirooxindoles through a three-component [3+2] cycloaddition
Guo, Jiaomei
Zhao, Yang
Fang, Dongmei
Wang, Qilin
Bu, Zhanwei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (33) : 6025 - 6034
[37] POLAROGRAPHIC INVESTIGATIONS AND MECHANISM OF THE ELECTROCHEMICAL REDUCTION OF CIS-OCTAHYDRO-PYRIDO[2,1-B]QUINAZOLIN-11-ONES AND TRANS-OCTAHYDRO-PYRIDO[2,1-B]QUINAZOLIN-11-ONES AND PYRROLO[2,1-B]QUINAZOLIN-11-ONES
PRICKEN, A
FRANKE, P
HUBER, I
FULOP, F
PFLEGEL, P
BERNATH, G
PHARMAZIE, 1990, 45 (10): : 740 - 747
[38] SYNTHESIS AND REACTIVITY OF 2-CHLORO-3-FORMYLPYRIDO[2,1-a]ISOQUINOLINE DERIVATIVE. A NOVEL ROUTES TO PYRAZOLO[3′,4′:4,5]PYRIDO[2,1-a]ISOQUINOLINE AND ISOQUINOLINO[2,1-g][1,6]NAPHTHYRIDINES
Hassaneen, Hamdi M.
Wardkhan, Wagnat W.
Mohammed, Yasmin Sh.
HETEROCYCLES, 2012, 85 (12) : 2933 - 2947
[39] SIMPLE AND EFFECTIVE SYNTHESIS OF PYRIDO[2,1-B]THIAZINES
MCCABE, RW
YOUNG, DW
DAVIES, GM
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (09) : 395 - 396
[40] Synthesis of sulfones in the pyrrolo[2,1-b]thiazole series
Tverdokhlebov, AV
Andrushko, AP
Tolmachev, AA
SYNTHESIS-STUTTGART, 2006, 9 (09): : 1433 - 1436

← 1 2 3 4 5 →