Synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives

Ju Hyeon Park; Jinjae Park; Cheol Hong Cheon

doi:10.1039/d3ob00056g

Synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives

Ju Hyeon Park, Jinjae Park, Cheol Hong Cheon

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

A protocol for the synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives was developed via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives. The synthetic utility of this methodology was illustrated by the concise synthesis of dihydropaullone, a partially saturated analog of paullone. Furthermore, the indoline scaffold could be further converted to the corresponding indoles and other indole-fused heterocycles.

Original language	English
Pages (from-to)	1647-1652
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	21
Issue number	8
DOIs	https://doi.org/10.1039/d3ob00056g
Publication status	Published - 2023 Jan 27

Bibliographical note

Funding Information:
This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2021R1A2C1012984, NRF-2021R1A5A6002803 (Center for New Directions in Organic Synthesis)).

Publisher Copyright:
© 2023 The Royal Society of Chemistry.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/d3ob00056g

Cite this

@article{e9caa568e15d4d1988006bee21da6559,

title = "Synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives",

abstract = "A protocol for the synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives was developed via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives. The synthetic utility of this methodology was illustrated by the concise synthesis of dihydropaullone, a partially saturated analog of paullone. Furthermore, the indoline scaffold could be further converted to the corresponding indoles and other indole-fused heterocycles.",

author = "Park, {Ju Hyeon} and Jinjae Park and Cheon, {Cheol Hong}",

note = "Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2021R1A2C1012984, NRF-2021R1A5A6002803 (Center for New Directions in Organic Synthesis)). Publisher Copyright: {\textcopyright} 2023 The Royal Society of Chemistry.",

year = "2023",

month = jan,

day = "27",

doi = "10.1039/d3ob00056g",

language = "English",

volume = "21",

pages = "1647--1652",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "8",

}

TY - JOUR

T1 - Synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives

AU - Park, Ju Hyeon

AU - Park, Jinjae

AU - Cheon, Cheol Hong

N1 - Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2021R1A2C1012984, NRF-2021R1A5A6002803 (Center for New Directions in Organic Synthesis)). Publisher Copyright: © 2023 The Royal Society of Chemistry.

PY - 2023/1/27

Y1 - 2023/1/27

N2 - A protocol for the synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives was developed via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives. The synthetic utility of this methodology was illustrated by the concise synthesis of dihydropaullone, a partially saturated analog of paullone. Furthermore, the indoline scaffold could be further converted to the corresponding indoles and other indole-fused heterocycles.

AB - A protocol for the synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives was developed via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives. The synthetic utility of this methodology was illustrated by the concise synthesis of dihydropaullone, a partially saturated analog of paullone. Furthermore, the indoline scaffold could be further converted to the corresponding indoles and other indole-fused heterocycles.

UR - http://www.scopus.com/inward/record.url?scp=85147717767&partnerID=8YFLogxK

U2 - 10.1039/d3ob00056g

DO - 10.1039/d3ob00056g

M3 - Article

C2 - 36723252

AN - SCOPUS:85147717767

SN - 1477-0520

VL - 21

SP - 1647

EP - 1652

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 8

ER -

Synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this