Novel intramolecular aza-Diels-Alder reaction: a facile synthesis of trans-fused 5H-chromeno[2,3-c]acridine derivatives

被引：18

作者：

Reddy, B. V. Subba ^{[1
]}

Antony, Aneesh ^{[1
]}

Yadav, J. S. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Discovery Lab, Div Organ Chem 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 23期

关键词：

Intramolecular cycloaddition; Alkene-tethered chromene-3-aldehyde; Lewis acid; Chromenoacridines; POTASSIUM CHANNEL OPENERS; ANTIHYPERTENSIVE ACTIVITY;

D O I：

10.1016/j.tetlet.2010.04.018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel series of 5H-chromeno[2,3-c]acridine derivatives has been prepared through the intramolecular aza-Diels-Alder reaction of alkene-tethered chromene-3-carboxaldehyde with various aromatic amines. This is the first example of the preparation of pentacyclic poly aromatic compounds in a single-step operation at ambient temperature. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3071 / 3074

页数：4

共 50 条

[41] A Facile Synthesis of Benzofuro[2,3-c]quinolines via a Multicomponent Reaction and Staudinger-Aza-Wittig-Dehydroaromatization Sequence
Wei, Jie
Nie, Bing-Jie
Peng, Rong
Cheng, Xiao-Hong
Wang, Song
He, Ping
SYNLETT, 2016, 27 (04) : 626 - 630
[42] A new methodology of intramolecular hetero Diels-Alder reaction with β-alkoxy-substituted conjugated nitroalkenes as heterodienes:: stereoselective one-pot synthesis of trans-fused bicyclic γ-lactones
Wada, E
Yoshinaga, M
TETRAHEDRON LETTERS, 2003, 44 (43) : 7953 - 7956
[43] One-pot synthesis of cyclopentane-fused 5′-aryl-4-cycloalkylamino-2,2′-bipyridines via the aza-Diels-Alder/SNipso reactions
Krinochkin, Alexey P.
Starnovskaya, Ekaterina S.
Valieva, Maria I.
Kopchuk, Dmitry S.
Santra, Sougata
Slepukhin, Pavel A.
Zyryanov, Grigory V.
Majee, Adinath
Chupakhin, Oleg N.
MENDELEEV COMMUNICATIONS, 2022, 32 (04) : 449 - 451
[44] Synthesis of pyrazoles and fused pyrazoles. Novel synthesis of pyrano[2,3-c]pyrazole, thieno[2,3-c]pyrazole and pyrazolo[3,4-b]pyridine derivatives
Ibrahim, MKA
Elghandour, AHH
AbdelSayed, GSM
Fattah, ASMA
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1997, 74 (03) : 206 - 208
[45] Synthesis of 5H-chromeno[3,4-c]pyridine derivatives through ruthenium-catalyzed [2+2+2] cycloaddition
Parisot, William
Huvelle, Steve
Haddad, Mansour
Lefevre, Guillaume
Phansavath, Phannarath
Ratovelomanana-Vidal, Virginie
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (05) : 1309 - 1315
[46] Lipase-catalyzed asymmetric synthesis of naphtho[2,3-c]furan-1(3H)-one derivatives by a one-pot dynamic kinetic resolution/intramolecular Diels-Alder reaction: Total synthesis of (-)-himbacine
Sugiyama, Koji
Kawanishi, Shinji
Oki, Yasuhiro
Kamiya, Marin
Hanada, Ryosuke
Egi, Masahiro
Akai, Shuji
BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (07) : 1378 - 1386
[47] One-Pot Synthesis of Novel Functionalized Fused Pyridine Derivatives via Consecutive Pyrrolidine Ring-Closure/Ring-Opening/ Formal Aza-Diels-Alder Reactions
Rizbayeva, Tanzilya
Smolobochkin, Andrey
Gazizov, Almir S.
Voronina, Julia
V. Syakaev, Viktor
Strelnik, Anna G.
Litvinov, Igor
Burilov, Alexander R.
Pudovik, Michail
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (17): : 11350 - 11361
[48] A New Approach to Di- and Tetrasubstituted 2,3-Dihydropyridin-4(1H)-ones through Aza-Diels-Alder Reaction Promoted by Silicon Tetrachloride
Massa, Antonio
de Sio, Vincenzo
Villano, Rosaria
Acocella, M. Rosaria
Palombi, Laura
Sellitto, Giusi
Peduto, Antonella
Filosa, Rosanna
De Capraris, Paolo
Scettri, Arrigo
SYNTHESIS-STUTTGART, 2009, (04): : 643 - 649
[49] Facile synthesis of pyrazino[2,3-e][1,4]diazepine derivatives via the intramolecular aza-Wittig reaction
Okawa, T
Eguchi, S
TETRAHEDRON LETTERS, 1996, 37 (01) : 81 - 84
[50] Facile synthesis of pyrazino[2,3-e][1,4]diazepine derivatives via the intramolecular aza-Wittig reaction
Okawa, T.
Eguchi, S.
Tetrahedron Letters, 37 (01):

← 1 2 3 4 5 →