A Base-Promoted Annulation Cascade: One-Pot Construction of C2-Spiropseudoindoxyls from 2-Nitrobenzaldehydes and Sulfonyl Hydrazones

20260 citationsJournal Article

Authors

Renhao Chen · Qingdao University of Science and Technology

Lidan Cheng · Materials Development (United States)

Feifei Xin · Qingdao University of Science and Technology

Luqian He · Qingdao University of Science and Technology

Binbin Tian · Qingdao University of Science and Technology

Yan Zhou · Qingdao University of Science and Technology

Cui Lv

Abstract

A metal- and oxidant-free protocol for the construction of diverse C2-spiropseudoindoxyl derivatives from 2-nitrobenzaldehydes and readily prepared sulfonyl hydrazones has been developed. Mechanistic studies suggest an intramolecular addition/S<sub>N</sub>Ar/1,5-H shift sequence. This strategy delivers valuable C2-spiro-piperidine and -azetidine indolin-3-one scaffolds for bioactive molecule modification.

Topics & Keywords

Sulfur-Based Synthesis Techniques Oxidative Organic Chemistry Reactions Catalytic C–H Functionalization Methods

Publication Details

Published in: The Journal of Organic Chemistry

Volume 91, Issue 12, pp. 4220-4227

DOI: 10.1021/acs.joc.5c02977

Field-Weighted Citation Impact: 0.00

Command Palette

A Base-Promoted Annulation Cascade: One-Pot Construction of C2-Spiropseudoindoxyls from 2-Nitrobenzaldehydes and Sulfonyl Hydrazones

Authors

Abstract

Topics & Keywords

Publication Details