The improved synthesis, diels-alder reactions, and desulfuration of trithio-1,8-naphthalic anhydride

Tian Bao Huang; Xuhong Qian; Zhi Fu Tao; Ke Wang; Gong Hua Song; Ling Fei Liu

doi:10.1002/(SICI)1098-1071(1999)10:2<141::AID-HC7>3.0.CO;2-B

The improved synthesis, diels-alder reactions, and desulfuration of trithio-1,8-naphthalic anhydride

Tian Bao Huang^*
, Xuhong Qian
, Zhi Fu Tao
, Ke Wang
, Gong Hua Song
, Ling Fei Liu

^*Corresponding author for this work

East China University of Science and Technology

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

5 Scopus citations

Abstract

In the presence of a strong Lewis base, such as Et₃N, trithio-1,8-naphthalic anhydride (3) is easily oxidized. Two improved syntheses of trithio-1,8-naphthalic anhydride (3) are described. Trithio-1,8-naphthalic anhydride (3) undergoes Diels-Alder reactions with electron-deficient alkenes to give novel fused heterocyclic compounds (6-11) that then can undergo a novel, gradual desulfuration dimerization with triethyl phosphite to afford 12 and its analogs 13 and 14. The structures of 6-14 are confirmed by microanalysis, IR, and NMR spectroscopy, and MS.

Original language	English
Pages (from-to)	141-146
Number of pages	6
Journal	Heteroatom Chemistry
Volume	10
Issue number	2
DOIs	https://doi.org/10.1002/(SICI)1098-1071(1999)10:2<141::AID-HC7>3.0.CO;2-B
State	Published - 1999
Externally published	Yes

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10.1002/(SICI)1098-1071(1999)10:2<141::AID-HC7>3.0.CO;2-B

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title = "The improved synthesis, diels-alder reactions, and desulfuration of trithio-1,8-naphthalic anhydride",

abstract = "In the presence of a strong Lewis base, such as Et3N, trithio-1,8-naphthalic anhydride (3) is easily oxidized. Two improved syntheses of trithio-1,8-naphthalic anhydride (3) are described. Trithio-1,8-naphthalic anhydride (3) undergoes Diels-Alder reactions with electron-deficient alkenes to give novel fused heterocyclic compounds (6-11) that then can undergo a novel, gradual desulfuration dimerization with triethyl phosphite to afford 12 and its analogs 13 and 14. The structures of 6-14 are confirmed by microanalysis, IR, and NMR spectroscopy, and MS.",

author = "Huang, \{Tian Bao\} and Xuhong Qian and Tao, \{Zhi Fu\} and Ke Wang and Song, \{Gong Hua\} and Liu, \{Ling Fei\}",

year = "1999",

doi = "10.1002/(SICI)1098-1071(1999)10:2<141::AID-HC7>3.0.CO;2-B",

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T1 - The improved synthesis, diels-alder reactions, and desulfuration of trithio-1,8-naphthalic anhydride

AU - Huang, Tian Bao

AU - Qian, Xuhong

AU - Tao, Zhi Fu

AU - Wang, Ke

AU - Song, Gong Hua

AU - Liu, Ling Fei

PY - 1999

Y1 - 1999

N2 - In the presence of a strong Lewis base, such as Et3N, trithio-1,8-naphthalic anhydride (3) is easily oxidized. Two improved syntheses of trithio-1,8-naphthalic anhydride (3) are described. Trithio-1,8-naphthalic anhydride (3) undergoes Diels-Alder reactions with electron-deficient alkenes to give novel fused heterocyclic compounds (6-11) that then can undergo a novel, gradual desulfuration dimerization with triethyl phosphite to afford 12 and its analogs 13 and 14. The structures of 6-14 are confirmed by microanalysis, IR, and NMR spectroscopy, and MS.

AB - In the presence of a strong Lewis base, such as Et3N, trithio-1,8-naphthalic anhydride (3) is easily oxidized. Two improved syntheses of trithio-1,8-naphthalic anhydride (3) are described. Trithio-1,8-naphthalic anhydride (3) undergoes Diels-Alder reactions with electron-deficient alkenes to give novel fused heterocyclic compounds (6-11) that then can undergo a novel, gradual desulfuration dimerization with triethyl phosphite to afford 12 and its analogs 13 and 14. The structures of 6-14 are confirmed by microanalysis, IR, and NMR spectroscopy, and MS.

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DO - 10.1002/(SICI)1098-1071(1999)10:2<141::AID-HC7>3.0.CO;2-B

M3 - 文章

AN - SCOPUS:0000281635

SN - 1042-7163

VL - 10

SP - 141

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JO - Heteroatom Chemistry

JF - Heteroatom Chemistry

IS - 2

ER -

The improved synthesis, diels-alder reactions, and desulfuration of trithio-1,8-naphthalic anhydride

Abstract

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