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

[21] ROUTES TO PYRROLO[2,1-B]THIAZOLES - ROTATIONAL-ISOMERISM OF PYRROLO[2,1-B]-THIAZOLE-5-CARBALDEHYDES
BRINDLEY, JC
GILLON, DG
MEAKINS, GD
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (07): : 1255 - 1259
[22] Novel rearrangement of pyrrolo[2,1-c] [1,4]benzodiazepines into pyrrolo[2,1-b]quinazolinones, analogous of alkaloid, vasicinone
Jolivet-Fouchet, S
Fabis, F
Bovy, P
Ochsenbein, P
Rault, S
HETEROCYCLES, 1999, 51 (06) : 1257 - +
[23] SUBSTITUTION REACTIONS ON PYRROLO[2,1-B]THIAZOLES
CEDER, O
BEIJER, B
TETRAHEDRON, 1972, 28 (16) : 4341 - &
[24] Formylation and Bromination of Pyrrolo[2,1-a]isoquinoline Derivatives with Bromoisobutyrate and Dimethyl Sulfoxide
Li, Jia-Qin
Tan, Hui-Lin
Ma, Dan-Dan
Zhu, Xin-Xin
Cui, Hai-Lei
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15): : 10118 - 10128
[25] A novel approach to pyrrolo[2,1-b]thiazoles
Tverdokhlebov, AV
Resnyanska, EV
Tolmachev, AA
Andrushko, AP
SYNTHESIS-STUTTGART, 2003, (17): : 2632 - 2638
[26] SYNTHESIS OF 2-(3-COUMARINYL)PYRROLO[2,1-a[ISOQUINOLINE DERIVATIVES BY THE CHICHIBABIN REACTION
Kulikova, Yu. A.
Surikova, O. V.
Mikhailovskii, A. G.
Vakhrin, M. I.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 47 (03) : 290 - 293
[27] SYNTHESIS OF HEXAHYDROBENZO[F] AND HEXAHYDROBENZO[H]PYRROLO[2,1-A]-ISOQUINOLINE DERIVATIVES
GRANDE, MT
SOLLHUBER, MM
CHEMICA SCRIPTA, 1988, 28 (04): : 411 - 414
[28] Synthesis of new pyrrolo[2,1-b]quinazolinones by original rearrangement of pyrrolo[2,1-c][1,4]benzodiazepines.
Jolivet-Fouchet, S
Fabis, F
Bovy, P
Ochsenbein, P
Rault, S
TETRAHEDRON LETTERS, 1998, 39 (08) : 819 - 820
[29] Synthesis of 2-(3-coumarinyl)pyrrolo[2,1-a]isoquinoline derivatives by the chichibabin reaction
Yu. A. Kulikova
O. V. Surikova
A. G. Mikhailovskii
M. I. Vakhrin
Chemistry of Heterocyclic Compounds, 2011, 47 : 290 - 293
[30] Synthesis of pyrrolo[2,1-a]isoquinolines from activated acetylenes, benzoylnitromethanes, and isoquinoline
Yavari, Issa
Piltan, Mohammad
Moradi, Loghman
TETRAHEDRON, 2009, 65 (10) : 2067 - 2071

← 1 2 3 4 5 →