Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction

被引：7

作者：

Narayanarao, Manjunatha ^{[1
]}

Koodlur, Lokesh ^{[2
]}

Revanasiddappa, Vijayakumar G. ^{[3
]}

Gopal, Subramanya ^{[2
]}

Kamila, Susmita ^{[1
]}

机构：

[1] Visvesvaraya Technol Univ, East Point Coll Engn & Technol, Bangalore 560049, Karnataka, India

[2] Vijayanagara Sri Krishnadevaraya Univ, Dept Studies & Res Che, Bellary 583105, India

[3] Tumkur Univ, Univ Coll Sci, Dept Chem, BH Rd, Tumakuru 572103, India

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 12卷

关键词：

L-proline; ninhydrin; sarcosine; spiropyrrolidine; 5-vinylindazole; 5-vinylindole; ONE-POT SYNTHESIS; 3-COMPONENT; DERIVATIVES; INHIBITORS;

D O I：

10.3762/bjoc.12.288

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new series of spiropyrrolidine compounds containing indole/indazole moieties as side chains have been accomplished via a one-pot multicomponent synthesis. The method uses the 1,3-dipolar cycloaddition reaction between N-alkylvinylindole/indazole and azomethine ylides, prepared in situ from cyclic/acyclic amino acids. The 1,3-dipolar cycloaddition proceeds efficiently under thermal conditions to afford the regio- and stereospecific cyclic adducts.

引用

页码：2893 / 2897

页数：5

共 50 条

[1] A CONVENIENT SYNTHESIS OF MUSCIMOL BY A 1,3-DIPOLAR CYCLOADDITION REACTION
CHIARINO, D
NAPOLETANO, M
SALA, A
TETRAHEDRON LETTERS, 1986, 27 (27) : 3181 - 3182
[2] Synthesis of novel spirofused spiropyrrolidine 1,3-indanedione derivatives via 1,3-dipolar cycloaddition reactions
Ghandi, Mehdi
Kenari, Marziyeh Eshaghi
Abbasi, Alireza
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2020, 17 (03) : 567 - 576
[3] Synthesis of novel spirofused spiropyrrolidine 1,3-indanedione derivatives via 1,3-dipolar cycloaddition reactions
Mehdi Ghandi
Marziyeh Eshaghi Kenari
Alireza Abbasi
Journal of the Iranian Chemical Society, 2020, 17 : 567 - 576
[4] 1,3-DIPOLAR CYCLOADDITION REACTION OF AZIRIDINEDICARBOXIMIDE
OIDA, S
OHKI, E
CHEMICAL & PHARMACEUTICAL BULLETIN, 1968, 16 (04) : 764 - +
[5] Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides
Najera, Carmen
Miguel Sansano, Jose
PURE AND APPLIED CHEMISTRY, 2019, 91 (04) : 575 - 596
[6] A facile synthesis of novel polycyclic spiropyrrolidine oxindoles incorporating the 1,3-dipolar cycloaddition of azomethine ylides
Treuerne Balazs, Krisztina E.
Molnar, Mark
Madarasz, Zoltan
Nyerges, Miklos
SYNTHETIC COMMUNICATIONS, 2020, 50 (21) : 3245 - 3255
[7] Regioselective Synthesis of Nitrofuran Containing Novel Spiropyrrolidine Library through 1,3-Dipolar Cycloaddition Reactions
Mallya, Sahana
Kalluraya, Balakrishna
Girisha, K. S.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (02) : 527 - 531
[8] Synthesis of spiroisoxazolines by 1,3-dipolar cycloaddition
Micuch, P
Fisera, L
Ondrus, V
Ertl, P
MOLECULES, 1997, 2 (03) : 57 - 61
[9] Novel synthesis of pyrroloquinolizidines via a 1,3-dipolar cycloaddition reaction
Qian, Xuelei
Angle, Steven R.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[10] Synthesis and Characterization of Isoxazolidine Derivatives by 1,3-Dipolar Cycloaddition Reaction
Al-Ghorbani, Mohammad
Al-Timari, Usama S.
Fadh, Taha A.
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 29 (02) : 131 - 137

← 1 2 3 4 5 →