Synthesis of Sterically Protected Isoindoles from ortho-Phthalaldehyde-Reference-Cited by-同舟云学术

Synthesis of Sterically Protected Isoindoles from ortho-Phthalaldehyde

Published:2018-01 Issue:01 Volume:02 Page:0050-0057
ISSN:2509-9396
Container-title:SynOpen
language:en
Short-container-title:SynOpen

Author:

Nakao Michiyasu¹,Nishikiori Nanako¹,Nakamura Akihito¹,Miyagi Murasaki¹,Shibata Nao¹,Kitaike Syuji¹,Fukui Makoto²,Ito Hiro-O²,Sano Shigeki¹

Affiliation:

1. Graduate School of Pharmaceutical Sciences, Tokushima University

2. Department of Preventive Dentistry, Institute of Biomedical Sciences, Tokushima University Graduate School

Abstract

o-Phthalaldehyde (OPA) reacts with O-protected tris(hydroxyalkyl)aminomethanes in the presence of 1-propanethiol to afford a novel class of stable isoindoles. Steric protection provided by the bulkiness of C 3-symmetric primary amines derived from tris(hydroxymethyl)aminomethane could be significant for the stabilization of 1-alkylthio-2-alkyl-substituted isoindoles derived from OPA. A plausible reaction mechanism is proposed to explain the formation of the isoindole and an isoindolin-1-one by-product.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Materials Science (miscellaneous),Biomaterials,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0036-1591932.pdf

Cited by 3 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Synthesis of Novel Phosphorus-Substituted Stable Isoindoles by a Three-Component Coupling Reaction of ortho-Phthalaldehyde, 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-Oxide, and Primary Amines;SynOpen;2023-08

2. Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks;Beilstein Journal of Organic Chemistry;2019-03-19

3. Pyrrole ring closure reactions in the synthesis of isoindoles (microreview);Chemistry of Heterocyclic Compounds;2018-10