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I 2 -Promoted gem -Diarylethene Involved Aza-Diels-Alder Reaction and Wagner-Meerwein Rearrangement: Construction of 2,3,4-Trisubstituted Pyrimido[1,2- b ]indazole Skeletons.

Authors :
Zhou Y
Lei SG
Wang LS
Ma JT
Yu ZC
Wu YD
Wu AX
Source :
Organic letters [Org Lett] 2023 May 19; Vol. 25 (19), pp. 3386-3390. Date of Electronic Publication: 2023 May 08.
Publication Year :
2023

Abstract

A [3 + 1 + 2] cyclization-rearrangement reaction scheme was developed to synthesize pyrimido[1,2- b ]indazoles from aryl methyl ketones, 3-aminoindazoles, and gem -diarylethenes. This metal-free process proceeds via a sequential aza-Diels-Alder reaction and Wagner-Meerwein rearrangement, and a possible reaction mechanism was demonstrated based on control experiments. This method exhibits good substrate compatibility and allows simple reaction conditions. Moreover, the products display significant aggregation-induced emission characteristics after simple modifications.

Details

Language :
English
ISSN :
1523-7052
Volume :
25
Issue :
19
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
37154544
Full Text :
https://doi.org/10.1021/acs.orglett.3c00886