An easy and efficient method for the synthesis of 2,2-dialkyl-3-nitrochromene

Ming Chung Yan; Yeong Jiunn Jang; Ching Fa Yao

doi:10.1016/S0040-4039(01)00284-2

An easy and efficient method for the synthesis of 2,2-dialkyl-3-nitrochromene

Ming Chung Yan
, Yeong Jiunn Jang
, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

63 Citations (Scopus)

Abstract

Reactions of salicylaldehyde 1, 1,4-diazabicyclo[2.2.2]octane (DABCO), with β-nitrostyrenes 2, 4, 12, 14, and 16, respectively, in the absence of solvent at 40°C gave high yields of 3-nitro-chromenes. Only 96% of trans-3-nitro-4-hydroxyflavans 7 or 98% of 10 were isolated when compounds 6 or 9 reacted with 1 and DABCO under similar conditions. When the reaction temperature was increased to 90°C, 7 and 10 underwent dehydration to generate 74% of 8 and 89% of 11.

Original language	English
Pages (from-to)	2717-2721
Number of pages	5
Journal	Tetrahedron Letters
Volume	42
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(01)00284-2
Publication status	Published - 2001 Apr 2

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)00284-2

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title = "An easy and efficient method for the synthesis of 2,2-dialkyl-3-nitrochromene",

abstract = "Reactions of salicylaldehyde 1, 1,4-diazabicyclo[2.2.2]octane (DABCO), with β-nitrostyrenes 2, 4, 12, 14, and 16, respectively, in the absence of solvent at 40°C gave high yields of 3-nitro-chromenes. Only 96\% of trans-3-nitro-4-hydroxyflavans 7 or 98\% of 10 were isolated when compounds 6 or 9 reacted with 1 and DABCO under similar conditions. When the reaction temperature was increased to 90°C, 7 and 10 underwent dehydration to generate 74\% of 8 and 89\% of 11.",

author = "Yan, \{Ming Chung\} and Jang, \{Yeong Jiunn\} and Yao, \{Ching Fa\}",

note = "Funding Information: Financial support of this work by the National Science Council of the Republic of China is gratefully acknowledged.",

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T1 - An easy and efficient method for the synthesis of 2,2-dialkyl-3-nitrochromene

AU - Yan, Ming Chung

AU - Jang, Yeong Jiunn

AU - Yao, Ching Fa

N1 - Funding Information: Financial support of this work by the National Science Council of the Republic of China is gratefully acknowledged.

PY - 2001/4/2

Y1 - 2001/4/2

N2 - Reactions of salicylaldehyde 1, 1,4-diazabicyclo[2.2.2]octane (DABCO), with β-nitrostyrenes 2, 4, 12, 14, and 16, respectively, in the absence of solvent at 40°C gave high yields of 3-nitro-chromenes. Only 96% of trans-3-nitro-4-hydroxyflavans 7 or 98% of 10 were isolated when compounds 6 or 9 reacted with 1 and DABCO under similar conditions. When the reaction temperature was increased to 90°C, 7 and 10 underwent dehydration to generate 74% of 8 and 89% of 11.

AB - Reactions of salicylaldehyde 1, 1,4-diazabicyclo[2.2.2]octane (DABCO), with β-nitrostyrenes 2, 4, 12, 14, and 16, respectively, in the absence of solvent at 40°C gave high yields of 3-nitro-chromenes. Only 96% of trans-3-nitro-4-hydroxyflavans 7 or 98% of 10 were isolated when compounds 6 or 9 reacted with 1 and DABCO under similar conditions. When the reaction temperature was increased to 90°C, 7 and 10 underwent dehydration to generate 74% of 8 and 89% of 11.

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DO - 10.1016/S0040-4039(01)00284-2

M3 - Article

AN - SCOPUS:0035795002

SN - 0040-4039

VL - 42

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

An easy and efficient method for the synthesis of 2,2-dialkyl-3-nitrochromene

Abstract

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