New Efficient Synthesis of 2-Substituted 5,6,7,8-Tetrahydro-benzo-thieno[2, 3-d]pyrimidin-4(3H)-ones

Ming Wu Ding; Shang Jun Yang; Jing Zhu

doi:10.1055/s-2003-44358

New Efficient Synthesis of 2-Substituted 5,6,7,8-Tetrahydro-benzo-thieno[2, 3-d]pyrimidin-4(3H)-ones

Ming Wu Ding, Shang Jun Yang, Jing Zhu

Central China Normal University

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

45 Scopus citations

Abstract

The carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with secondary amines to give 2-dialkylamino-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones 6 in presence of catalytic EtO^-Na⁺. Reactions of 4 with phenols or ROH in presence of catalytic K₂CO₃ or RO ^-Na⁺ gave 2-aryl(alkyl)oxy-5,6,7,8-tetrahydro- benzothieno[2,3-d]pyrimidin-4(3H)-ones 6 in satisfactory yields. The effects of the nucleophiles on cyclization have been investigated.

Original language	English
Pages (from-to)	75-79
Number of pages	5
Journal	Synthesis (Germany)
Issue number	1
DOIs	https://doi.org/10.1055/s-2003-44358
State	Published - 5 Jan 2004
Externally published	Yes

Keywords

Aza-Wittig reaction
Benzothieno[2,3-d]pyrimidin-4(3H)-ones
Carbodiimide
Iminophosphorane
Synthesis

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10.1055/s-2003-44358

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title = "New Efficient Synthesis of 2-Substituted 5,6,7,8-Tetrahydro-benzo-thieno[2, 3-d]pyrimidin-4(3H)-ones",

abstract = "The carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with secondary amines to give 2-dialkylamino-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones 6 in presence of catalytic EtO-Na+. Reactions of 4 with phenols or ROH in presence of catalytic K2CO3 or RO -Na+ gave 2-aryl(alkyl)oxy-5,6,7,8-tetrahydro- benzothieno[2,3-d]pyrimidin-4(3H)-ones 6 in satisfactory yields. The effects of the nucleophiles on cyclization have been investigated.",

keywords = "Aza-Wittig reaction, Benzothieno[2,3-d]pyrimidin-4(3H)-ones, Carbodiimide, Iminophosphorane, Synthesis",

author = "Ding, \{Ming Wu\} and Yang, \{Shang Jun\} and Jing Zhu",

year = "2004",

month = jan,

day = "5",

doi = "10.1055/s-2003-44358",

language = "英语",

pages = "75--79",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "1",

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TY - JOUR

T1 - New Efficient Synthesis of 2-Substituted 5,6,7,8-Tetrahydro-benzo-thieno[2, 3-d]pyrimidin-4(3H)-ones

AU - Ding, Ming Wu

AU - Yang, Shang Jun

AU - Zhu, Jing

PY - 2004/1/5

Y1 - 2004/1/5

N2 - The carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with secondary amines to give 2-dialkylamino-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones 6 in presence of catalytic EtO-Na+. Reactions of 4 with phenols or ROH in presence of catalytic K2CO3 or RO -Na+ gave 2-aryl(alkyl)oxy-5,6,7,8-tetrahydro- benzothieno[2,3-d]pyrimidin-4(3H)-ones 6 in satisfactory yields. The effects of the nucleophiles on cyclization have been investigated.

AB - The carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with secondary amines to give 2-dialkylamino-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones 6 in presence of catalytic EtO-Na+. Reactions of 4 with phenols or ROH in presence of catalytic K2CO3 or RO -Na+ gave 2-aryl(alkyl)oxy-5,6,7,8-tetrahydro- benzothieno[2,3-d]pyrimidin-4(3H)-ones 6 in satisfactory yields. The effects of the nucleophiles on cyclization have been investigated.

KW - Aza-Wittig reaction

KW - Benzothieno[2,3-d]pyrimidin-4(3H)-ones

KW - Carbodiimide

KW - Iminophosphorane

KW - Synthesis

UR - https://www.scopus.com/pages/publications/0347319076

U2 - 10.1055/s-2003-44358

DO - 10.1055/s-2003-44358

M3 - 文章

AN - SCOPUS:0347319076

SN - 0039-7881

SP - 75

EP - 79

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 1

ER -

New Efficient Synthesis of 2-Substituted 5,6,7,8-Tetrahydro-benzo-thieno[2, 3-d]pyrimidin-4(3H)-ones

Abstract

Keywords

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