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

Ming Chung Yan, Yeong Jiunn Jang, Ching Fa Yao

Research output: Contribution to journalArticle

57 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 languageEnglish
Pages (from-to)2717-2721
Number of pages5
JournalTetrahedron Letters
Volume42
Issue number14
DOIs
Publication statusPublished - 2001 Apr 2

Fingerprint

Benzopyrans
Dehydration
Temperature
triethylenediamine
diazabicyclo(2.2.2)octane
salicylaldehyde

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

An easy and efficient method for the synthesis of 2,2-dialkyl-3-nitrochromene. / Yan, Ming Chung; Jang, Yeong Jiunn; Yao, Ching Fa.

In: Tetrahedron Letters, Vol. 42, No. 14, 02.04.2001, p. 2717-2721.

Research output: Contribution to journalArticle

Yan, Ming Chung ; Jang, Yeong Jiunn ; Yao, Ching Fa. / An easy and efficient method for the synthesis of 2,2-dialkyl-3-nitrochromene. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 14. pp. 2717-2721.
@article{00e48065cfa845e8959f7bc18f3b5bfb,
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}",
year = "2001",
month = "4",
day = "2",
doi = "10.1016/S0040-4039(01)00284-2",
language = "English",
volume = "42",
pages = "2717--2721",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "14",

}

TY - JOUR

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

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.

UR - http://www.scopus.com/inward/record.url?scp=0035795002&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035795002&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)00284-2

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

M3 - Article

AN - SCOPUS:0035795002

VL - 42

SP - 2717

EP - 2721

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 14

ER -