One-Pot, Two-Step Synthesis of Highly Functionalized 4-Indolyl/Pyrrolyl-Chromanes via a para -Quinone Methide Formation-1,8-Addition Sequence

被引：0

作者：

Khatoon, Rafia ^{[1
,2
]}

Jandial, Tanvi ^{[2
]}

Gupta, Anish ^{[2
]}

Kundan, Sujata ^{[2
]}

Sridharan, Vellaisamy ^{[2
,3
]}

机构：

[1] Baba Ghulam Shah Badshah Univ, Sch Engn & Technol, Dept Appl Sci, Rajouri 185234, J&K, India

[2] Cent Univ Jammu, Dept Chem & Chem Sci, Jammu 181143, J&K, India

[3] Univ Hyderabad, Sch Chem, Hyderabad 500046, India

来源：

SYNTHESIS-STUTTGART | 2025年 / 57卷 / 01期

关键词：

heterocycles; 4-indolyl-chromanes; 4-pyrrolyl-chromanes; p-quinone methide; 1,8-addition; DOMINO REACTIONS; 1,6-ADDITION; ACID;

D O I：

10.1055/a-2371-3579

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot, two-step synthesis of structurally diverse 4-indolyl-/pyrrolyl-chromanes was developed starting from o-propargylated salicylaldehydes, 2,6-dialkylphenols and indoles/pyrrole. This process begins with a sequential secondary amine-catalyzed formation of p-quinone methides followed by Br & oslash;nsted acid catalyzed 1,8-addition with indoles/pyrrole to access the functionalized chromanes in high yields (up to 91%). This sequential reaction generates three new C-C bonds, shows high step- and atom-economy with only one molecule of water as the side product and gives access to complex molecular frameworks without the need for the isolation of the intermediates.

引用

页码：218 / 228

页数：11