Bismuth(III) chloride-catalyzed intramolecular hetero Diels-Alder reaction:: Application to the synthesis of tetrahydrochromano[4,3-b]quinoline derivatives

被引：0

作者：

Sabitha, G ^{[1
]}

Reddy, EV ^{[1
]}

Yadav, JS ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2001年 / 13期

关键词：

hetero Diels-Alder-reaction; bismuth(III) chloride; catalysis; tetrahydrochromanoquinolines;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular [4+2] cycloaddition reaction of aldimines derived from aromatic amines and O-allyl derivatives of salicylic aldehydes was efficiently catalyzed by BiCl3 to afford the corresponding tetrahydrochromano[4,3-b]quinolines in excellent yields. The products are isolated as 1:1 mixture of diastereoisomers.

引用

页码：1979 / 1984

页数：6

共 50 条

[31] Synthesis of New Pyrano[2′,3′:5,6]chromeno[4,3-b]quinolin-4-ones via Aza-Diels-Alder Reaction
Kumar, Bejjanki Naveen
Venkatesham, Akkaladevi
Nagaiah, Kommu
Babu, Nanubolu Jagadeesh
HELVETICA CHIMICA ACTA, 2015, 98 (03) : 417 - 426
[32] PERISELECTIVE, LEWIS ACID-INDUCED INTRAMOLECULAR DIELS-ALDER REACTION OF CONJUGATED CARBODIIMIDES - EFFICIENT SYNTHESIS OF NITROGEN-HETEROCYCLES, INDOLO[2,3-B]QUINOLINES AND PYRIDO[2,3-B]INDOLE
SAITO, T
OHMORI, H
OHKUBO, T
MOTOKI, S
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (24) : 1802 - 1803
[33] Photochemically catalyzed Diels-Alder reaction of azadienes with 2,3-dihydrofuran by 2,4,6-triphenylpyrylium salt: Synthesis of styrylfuroquinoline derivatives
Zhang, W
Guo, YP
Yang, L
Liu, L
CHINESE CHEMICAL LETTERS, 2005, 16 (05) : 575 - 578
[34] Photochemically Catalyzed Diels-Alder Reaction of Azadienes with 2,3-Dihydrofuran by 2,4,6-Triphenylpyrylium Salt:Synthesis of Styrylfuroquinoline Derivatives
Wei ZHANG
Chinese Chemical Letters, 2005, (05) : 575 - 578
[35] Microwave-induced domino-Knoevenagel-hetero Diels-Alder reaction-an easy route to di[1]benzopyrano[2,3-b:4′,3′-d]pyridine
Biswas, Pritam
Ghosh, Jaydip
Maiti, Sourav
Bandyopadhyay, Chandrakanta
TETRAHEDRON LETTERS, 2014, 55 (50) : 6882 - 6886
[36] FeCl3-Catalyzed Synthesis of 2-Methyl-4-Substituted-1,2,3,4-Tetrahydroquinoline Derivatives by the Imino Diels-Alder Reaction
Chen, Ye
Lee, Yong Rok
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (07): : 2485 - 2488
[37] Domino Knoevenagel hetero-Diels-Alder reactions:: a stereoselective synthesis of sugar fused furo[3,2-b]pyrano[4,3-d]pyran derivatives
Yadav, JS
Reddy, BVS
Narsimhaswamy, D
Lakshmi, PN
Narsimulu, K
Srinivasulu, G
Kunwar, AC
TETRAHEDRON LETTERS, 2004, 45 (17) : 3493 - 3497
[38] Synthesis of Tetrahydrothiopyrano[2,3-b]indole [60]Fullerene Derivatives via Hetero-Diels-Alder Reaction of C60 and ,-Unsaturated Indole-2-thiones
Moghaddam, Firouz Matloubi
Ghanbari, Bahram
Behzadi, Masoumeh
Baghersad, Mohammad Hadi
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (02) : 911 - 915
[39] Domino Knoevenagel-hetero-Diels-Alder reactions: a stereoselective synthesis of sugar-annulated furo[3,2-b] pyrano[4,3-d]pyran derivatives
Yadav, J. S.
Reddy, B. V. Subba
Gopal, A. V. Hara
Rao, R. Nageshwar
Somaiah, R.
Reddy, P. Purushotham
Kunwar, A. C.
TETRAHEDRON LETTERS, 2010, 51 (17) : 2305 - 2308
[40] ORGN 159-One pot Diels-Alder reaction of a,b-unsaturated thio-oxindoles with dialkylacetylenicdiesters and cyclic dienophiles for synthesis of novel thiopyrano [2,3-b] indole derivatives(4a-t)
Pirani, Parisa
Moghaddam, Firouz Matloubi
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237

← 1 2 3 4 5 →