Efficient one-pot synthesis of novel and diverse tetrahydroquinolines bearing pyranopyrazoles using organocatalyzed domino Knoevenagel/hetero Diels-Alder reactions

被引：17

作者：

Pandit, Rameshwar Prasad ^{[1
]}

Lee, Yong Rok ^{[1
]}

机构：

[1] Yeungnam Univ, Sch Chem Engn, Kyongsan 712749, South Korea

来源：

MOLECULAR DIVERSITY | 2014年 / 18卷 / 01期

基金：

新加坡国家研究基金会;

关键词：

Tetrahydroquinolines; Pyrazolones; Aminoaldehydes; Knoevenagel condensation; Hetero Diels-Alder reaction; INTRAMOLECULAR CYCLIZATION; FACILE SYNTHESIS; INHIBITORS; DERIVATIVES; PROTEIN; VIRANTMYCIN; DISCOVERY; QUINOLINE; STRAIN; PYRANO;

D O I：

10.1007/s11030-013-9482-6

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new synthetic route to biologically interesting diverse tetrahydroquinolines bearing pyranopyrazoles was developed by reacting pyrazolones and ,-dialkylated aminobenzaldehydes in the presence of EDDA. The key strategy underlying the methodology used was the domino Knoevenagel/hetero Diels-Alder reaction. This synthetic method provides a variety of novel tetrahydroquinolines in good yields.

引用

下载

页码：39 / 50

页数：12

共 50 条

[31] Zirconium oxide (NP) - ionic liquid as an efficient media for the domino Knoevenagel hetero Diels-Alder reaction with unactivated alkynes
Balalaie, Saeed
Poursaeed, Ali
Khoshkholgh, Malihe Javan
Bijanzadeh, Hamid Reza
Wolf, Eckardt
COMPTES RENDUS CHIMIE, 2012, 15 (04) : 283 - 289
[32] Hetero Diels-Alder reactions of nitrosoamidines: An efficient method for the synthesis of functionalized guanidines
Miller, CA
Batey, RA
ORGANIC LETTERS, 2004, 6 (05) : 699 - 702
[33] An efficient domino Knoevenagel/hetero-Diels-Alder route to some novel thiochromenoquinoline-fused polyheterocycles
Parmar, Narsidas J.
Labana, Balvantsingh M.
Barad, Hitesh A.
Kant, Rajni
Gupta, Vivek K.
MONATSHEFTE FUR CHEMIE, 2014, 145 (07): : 1179 - 1189
[34] An efficient domino Knoevenagel/hetero-Diels–Alder route to some novel thiochromenoquinoline-fused polyheterocycles
Narsidas J. Parmar
Balvantsingh M. Labana
Hitesh A. Barad
Rajni Kant
Vivek K. Gupta
Monatshefte für Chemie - Chemical Monthly, 2014, 145 : 1179 - 1189
[35] Inverse electron demand Diels-Alder reactions of heterodienes catalyzed by potassium hydrogen sulfate: Diastereoselective, one-pot synthesis of pyranobenzopyrans, furanobenzopyrans and tetrahydroquinolines derivatives
Kumar, RS
Nagarajan, R
Perumal, PT
SYNTHESIS-STUTTGART, 2004, (06): : 949 - 959
[36] Efficient synthesis of pentacyclic benzosultam-annulated thiopyranoindoles via domino Knoevenagel / intramolecular hetero-Diels-Alder reactions in water
Kiamehr, Mostafa
Khademi, Fahimeh
Jafari, Behzad
Langer, Peter
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (03) : 392 - 398
[37] Efficient synthesis of pyrano[2,3-c]coumarins via intramolecular domino Knoevenagel hetero-Diels-Alder reactions
Khoshkholgh, Malihe Javan
Lotfi, Minoo
Balalaie, Saeed
Rominger, Frank
TETRAHEDRON, 2009, 65 (21) : 4228 - 4234
[38] Efficient synthesis of pentacyclic benzosultam-annulated thiopyranoindoles via domino Knoevenagel / intramolecular hetero-Diels–Alder reactions in water
Mostafa Kiamehr
Fahimeh Khademi
Behzad Jafari
Peter Langer
Chemistry of Heterocyclic Compounds, 2020, 56 : 392 - 398
[39] Three-component tandem Knoevenagel/hetero Diels-Alder reactions total synthesis of (±)-preethulia coumarin
Appendino, G
Cravotto, G
Minassi, A
Palmisano, G
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (19) : 3711 - 3717
[40] An efficient synthesis of thiopyrano[5,6-c]coumarin/[6,5-c]-chromones through intramolecular domino Knoevenagel hetero Diels-Alder reactions
Jayashankaran, J
Manian, RDRS
Raghunathan, R
TETRAHEDRON LETTERS, 2006, 47 (13) : 2265 - 2270

← 1 2 3 4 5 →