Molybdenum oxides as highly effective dehydrative cyclization catalysts for the synthesis of oxazolines and thiazolines

Akira Sakakura; Rei Kondo; Kazuaki Ishihara

doi:10.1021/ol050543j

Molybdenum oxides as highly effective dehydrative cyclization catalysts for the synthesis of oxazolines and thiazolines

Akira Sakakura, Rei Kondo, Kazuaki Ishihara

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

86 Citations (Scopus)

Abstract

(Chemical Equation Presented) In the presence of molybdenum oxide the dehydrative cyclization of N-acylserines, N-acylthreonines, and N-acylcysteines can be carried out under Dean-Stark conditions in toluene to give oxazolines and thiazolines. The ammonium salts (NH₄)₆Mo ₇O₂₄·4H₂O and (NH₄) ₂MoO₄ have excellent catalytic activities for the dehydrative cyclization of serine and threonine derivatives, and the acetylacetonate complex MoO₂(acac)₂ has a remarkable catalytic activity for the dehydrative cyclization of cysteine derivatives. In addition, polyaniline-supported MoO₂(acac)₂ can easily be recovered and reused.

Original language	English
Pages (from-to)	1971-1974
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	10
DOIs	https://doi.org/10.1021/ol050543j
Publication status	Published - May 12 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol050543j

Cite this

@article{10b0e11f350841af99b8f2884228b2ae,

title = "Molybdenum oxides as highly effective dehydrative cyclization catalysts for the synthesis of oxazolines and thiazolines",

abstract = "(Chemical Equation Presented) In the presence of molybdenum oxide the dehydrative cyclization of N-acylserines, N-acylthreonines, and N-acylcysteines can be carried out under Dean-Stark conditions in toluene to give oxazolines and thiazolines. The ammonium salts (NH4)6Mo 7O24·4H2O and (NH4) 2MoO4 have excellent catalytic activities for the dehydrative cyclization of serine and threonine derivatives, and the acetylacetonate complex MoO2(acac)2 has a remarkable catalytic activity for the dehydrative cyclization of cysteine derivatives. In addition, polyaniline-supported MoO2(acac)2 can easily be recovered and reused.",

author = "Akira Sakakura and Rei Kondo and Kazuaki Ishihara",

year = "2005",

month = may,

day = "12",

doi = "10.1021/ol050543j",

language = "English",

volume = "7",

pages = "1971--1974",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Molybdenum oxides as highly effective dehydrative cyclization catalysts for the synthesis of oxazolines and thiazolines

AU - Sakakura, Akira

AU - Kondo, Rei

AU - Ishihara, Kazuaki

PY - 2005/5/12

Y1 - 2005/5/12

N2 - (Chemical Equation Presented) In the presence of molybdenum oxide the dehydrative cyclization of N-acylserines, N-acylthreonines, and N-acylcysteines can be carried out under Dean-Stark conditions in toluene to give oxazolines and thiazolines. The ammonium salts (NH4)6Mo 7O24·4H2O and (NH4) 2MoO4 have excellent catalytic activities for the dehydrative cyclization of serine and threonine derivatives, and the acetylacetonate complex MoO2(acac)2 has a remarkable catalytic activity for the dehydrative cyclization of cysteine derivatives. In addition, polyaniline-supported MoO2(acac)2 can easily be recovered and reused.

AB - (Chemical Equation Presented) In the presence of molybdenum oxide the dehydrative cyclization of N-acylserines, N-acylthreonines, and N-acylcysteines can be carried out under Dean-Stark conditions in toluene to give oxazolines and thiazolines. The ammonium salts (NH4)6Mo 7O24·4H2O and (NH4) 2MoO4 have excellent catalytic activities for the dehydrative cyclization of serine and threonine derivatives, and the acetylacetonate complex MoO2(acac)2 has a remarkable catalytic activity for the dehydrative cyclization of cysteine derivatives. In addition, polyaniline-supported MoO2(acac)2 can easily be recovered and reused.

UR - http://www.scopus.com/inward/record.url?scp=19544377371&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=19544377371&partnerID=8YFLogxK

U2 - 10.1021/ol050543j

DO - 10.1021/ol050543j

M3 - Article

C2 - 15876032

AN - SCOPUS:19544377371

VL - 7

SP - 1971

EP - 1974

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -

Molybdenum oxides as highly effective dehydrative cyclization catalysts for the synthesis of oxazolines and thiazolines

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this