Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction.
J Org Chem
; 89(15): 10854-10866, 2024 Aug 02.
Article
em En
| MEDLINE
| ID: mdl-38993063
ABSTRACT
A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing o-hydroxyphenyl group. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 3-(o-hydroxyarylidene)indolin-2-ones in tetrahydrofuran at 60 °C resulted in unique functionalized spiro[cyclobuta[c]chromene-1,3'-indolines] in good yields and with high diastereoselectivity. However, the similar three-component reaction with 2-(5-halo-2-hydroxyarylidene)indolin-2-ones afforded unexpected chain products in satisfactory yields. In addition, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 2-(o-hydroxyarylidene)-1,3-indanediones in tetrahydrofuran at 60 °C resulted in complex indeno[2',1'5,6]pyrano[3,4-c]chromene derivatives in high yields and with high diastereoselectivity.
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MEDLINE
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En
Ano de publicação:
2024
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Article