Pyridine-Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine

被引：4

作者：

Zubenko, A. A. ^{[1
]}

Morkovnik, A. S. ^{[2
]}

Divaeva, L. N. ^{[2
]}

Kartsev, V. G. ^{[3
]}

Anisimov, A. A. ^{[4
]}

Suponitsky, K. Yu. ^{[5
]}

机构：

[1] North Caucasus Zonal Res Vet Inst, Rostovskoe Shosse, Novocherkassk 346421, Rostov Oblast, Russia

[2] Southern Fed Univ, Inst Phys & Organ Chem, Pr Stachki 194-2, Rostov Na Donu 344090, Russia

[3] InterBioScreen Ltd, Inst Skii Pr 7, Chernogolovka 142432, Moscow Oblast, Russia

[4] Mendeleev Univ Chem Technol Russia, Miusskaya Pl 9, Moscow 125047, Russia

[5] Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Ul Vavilova 28, Moscow 119991, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 55卷 / 01期

基金：

俄罗斯基础研究基金会;

关键词：

3,4-dihydro-nor-isoharmine; recyclization; 1,2-acyl rearrangement; 4(5)-acyl-9-methoxy-3-methyl-1,2-dihydroazepino[4,5-b]indoles; RING EXPANSION; RECYCLIZATION; 9-BROMOCOTARNINE; ROUTE;

D O I：

10.1134/S1070428019010081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Structural modification of 3,4-dihydro-nor-isoharmine through expansion of the dihydropyridine ring to dihydroazepine was accomplished in two stages including pyridine-azepine recyclization of the quaternized substrate by the action of phenacyl halides and their heterocyclic analogs. The recyclization process can be accompanied by 1,2-migration of the acyl group to give mixtures of 4-acyl-9-methoxy-3-methyl-1,2-dihydroazepino[4,5-b]indoles and their 5-acyl-substituted isomers. Factor influencing the recyclization direction and product ratio were analyzed.

引用

页码：74 / 82

页数：9

共 24 条

[1]

[Anonymous], 2014, AIMALL VERSION 14 11

[2]

[Anonymous], 2009, APEX2

[3]

Bader R. F., 1990, ENCY COMPUTATIONAL C

[4] Novel highly energetic pyrazoles: N-fluorodinitromethyl and N-[(difluoroamino)dinitromethyl] derivatives [J].

Dalinger, Igor L. ;

Shakhnes, Aleksandr Kh. ;

Monogarov, Konstantin A. ;

Suponitsky, Kyrill Yu. ;

Sheremetev, Aleksei B. .

MENDELEEV COMMUNICATIONS, 2015, 25 (06) :429-431

[5] The influence of halogen type on structural features of compounds containing α-halo-α,α-dinitroethyl moieties [J].

Dmitrienko, Artem O. ;

Karnoukhova, Valentina A. ;

Potemkin, Aleksandr A. ;

Struchkova, Marina I. ;

Kryazhevskikh, Irina A. ;

Suponitsky, Kirill Yu. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (05) :532-539

[6] OLEX2: a complete structure solution, refinement and analysis program [J].

Dolomanov, Oleg V. ;

Bourhis, Luc J. ;

Gildea, Richard J. ;

Howard, Judith A. K. ;

Puschmann, Horst .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341

[7] About the evaluation of the local kinetic, potential and total energy densities in closed-shell interactions [J].

Espinosa, E ;

Alkorta, I ;

Rozas, I ;

Elguero, J ;

Molins, E .

CHEMICAL PHYSICS LETTERS, 2001, 336 (5-6) :457-461

[8] Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities [J].

Espinosa, E ;

Molins, E ;

Lecomte, C .

CHEMICAL PHYSICS LETTERS, 1998, 285 (3-4) :170-173

[9] High-density insensitive energetic materials: 2,4,6-tris(2-fluoro-2,2-dinitroethoxy)-1,3,5-triazine [J].

Gidaspov, Alexander A. ;

Bakharev, Vladimir V. ;

Suponitsky, Kyrill Yu. ;

Nikitin, Valery G. ;

Sheremetev, Aleksei B. .

RSC ADVANCES, 2016, 6 (106) :104325-104329

[10] A facile, one pot method for the synthesis of 4-acyl-1,2-dihydro-3-benzazepines, based on the ring expansion of natural and synthetic 3,4-dihydroisoquinoline pseudo bases [J].

Kartsev, Viktor G. ;

Zubenko, Alexander A. ;

Morkovnik, Anatolii S. ;

Divaeva, Ludmila N. .

TETRAHEDRON LETTERS, 2015, 56 (50) :6988-6993

← 1 2 3 →