Domino Reaction between Nitrosoarenes and Ynenones for Catalyst-Free Preparation of Indanone-Fused Tetrahydroisoxazoles

Abstract

A catalyst-free domino reaction to synthesize highly functionalized indanone-fused tetrahydro­isoxazole from easily accessed nitrosoarene and 1,6-ynenone with good chemo- and regioselectivity was disclosed. This unprecedented domino reaction represents a new strategy for multifunctionalization of an internal alkyne with nitrosoarene by formation of two rings and four bonds in a single operation.

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

“…In this study, they also disclosed that under high reaction temperature benzisoxazolines 4-99 could isomerize to dihydrobenzo­[ d ]­oxazoles 4-100 . Moreover, this aryne-nitrone cycloaddition protocol was utilized in many synthetic applications as well. − …”

Highlighting the Underrated Side of the High Profile Nitroso Entity as a Nucleophile

“…Its reaction with terminal alkynes 9 is a route towards to forming two rings and four new bonds in a single operation (Scheme 3). [44] …”

Transition‐Metal‐Free Synthesis of 1‐Indanone Skeleton: A Brief Update

“…Synthesis of organic compounds under uncatalyzed conditions is an important aspect in synthetic chemistry. Zhu and co‐workers employed 1,6‐ynenones 111 (containing both an internal alkyne and deficient C=C functional groups) and nitrosoarenes 112 for the synthesis of highly functionalized indanone derivatives 113 under catalyst‐free condition [64] . In general, 1,6‐ynenones with various substituents delivers the desired products in good yields.…”