Preparation of 5-acyl- and 5-aryl-substituted 1-(benzyloxy)pyrazoles via directed ortho-lithiation/transmetalation and palladium catalyzed cross- coupling

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Preparation of 5-acyl- and 5-aryl-substituted 1-(benzyloxy)pyrazoles via directed ortho-lithiation/transmetalation and palladium catalyzed cross- coupling. / Kristensen, Jesper Langgaard; Begtrup, M.; Vedsø, P.

In: Synthesis, No. 11, 01.11.1998, p. 1604-1608.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Kristensen, JL, Begtrup, M & Vedsø, P 1998, 'Preparation of 5-acyl- and 5-aryl-substituted 1-(benzyloxy)pyrazoles via directed ortho-lithiation/transmetalation and palladium catalyzed cross- coupling', Synthesis, no. 11, pp. 1604-1608.

APA

Kristensen, J. L., Begtrup, M., & Vedsø, P. (1998). Preparation of 5-acyl- and 5-aryl-substituted 1-(benzyloxy)pyrazoles via directed ortho-lithiation/transmetalation and palladium catalyzed cross- coupling. Synthesis, (11), 1604-1608.

Vancouver

Kristensen JL, Begtrup M, Vedsø P. Preparation of 5-acyl- and 5-aryl-substituted 1-(benzyloxy)pyrazoles via directed ortho-lithiation/transmetalation and palladium catalyzed cross- coupling. Synthesis. 1998 Nov 1;(11):1604-1608.

Author

Kristensen, Jesper Langgaard ; Begtrup, M. ; Vedsø, P. / Preparation of 5-acyl- and 5-aryl-substituted 1-(benzyloxy)pyrazoles via directed ortho-lithiation/transmetalation and palladium catalyzed cross- coupling. In: Synthesis. 1998 ; No. 11. pp. 1604-1608.

Bibtex

@article{a134f03f2daa439ab35b4d70c25e5faf,
title = "Preparation of 5-acyl- and 5-aryl-substituted 1-(benzyloxy)pyrazoles via directed ortho-lithiation/transmetalation and palladium catalyzed cross- coupling",
abstract = "Palladium(0) catalyzed cross-coupling of 1-(benzyloxy)pyrazol-5-ylzinc halides 3a,b, prepared by transmetalation of 1-(benzyloxy)-5-lithiopyrazole (2), with acyl chlorides produced 5 acyl-1-(benzyloxy)pyrazoles 4a-d in high yields. Similar coupling of the pyrazol-5-ylzinc halide with amino-, hydroxy- , methoxy-, fluoro-, nitro-, or formyl-substituted iodobenzene gave the corresponding 5-aryl-1-(benzyloxy)pyrazoles 5a-f, while coupling with iodothiophene, iodopyrazole or bromopyridine provided the corresponding 1- (benzyloxy)-5-heteroarylpyrazoles 6a-c.",
author = "Kristensen, {Jesper Langgaard} and M. Begtrup and P. Veds{\o}",
year = "1998",
month = nov,
day = "1",
language = "English",
pages = "1604--1608",
journal = "Synthesis",
issn = "0039-7881",
publisher = "GeorgThieme Verlag",
number = "11",

}

RIS

TY - JOUR

T1 - Preparation of 5-acyl- and 5-aryl-substituted 1-(benzyloxy)pyrazoles via directed ortho-lithiation/transmetalation and palladium catalyzed cross- coupling

AU - Kristensen, Jesper Langgaard

AU - Begtrup, M.

AU - Vedsø, P.

PY - 1998/11/1

Y1 - 1998/11/1

N2 - Palladium(0) catalyzed cross-coupling of 1-(benzyloxy)pyrazol-5-ylzinc halides 3a,b, prepared by transmetalation of 1-(benzyloxy)-5-lithiopyrazole (2), with acyl chlorides produced 5 acyl-1-(benzyloxy)pyrazoles 4a-d in high yields. Similar coupling of the pyrazol-5-ylzinc halide with amino-, hydroxy- , methoxy-, fluoro-, nitro-, or formyl-substituted iodobenzene gave the corresponding 5-aryl-1-(benzyloxy)pyrazoles 5a-f, while coupling with iodothiophene, iodopyrazole or bromopyridine provided the corresponding 1- (benzyloxy)-5-heteroarylpyrazoles 6a-c.

AB - Palladium(0) catalyzed cross-coupling of 1-(benzyloxy)pyrazol-5-ylzinc halides 3a,b, prepared by transmetalation of 1-(benzyloxy)-5-lithiopyrazole (2), with acyl chlorides produced 5 acyl-1-(benzyloxy)pyrazoles 4a-d in high yields. Similar coupling of the pyrazol-5-ylzinc halide with amino-, hydroxy- , methoxy-, fluoro-, nitro-, or formyl-substituted iodobenzene gave the corresponding 5-aryl-1-(benzyloxy)pyrazoles 5a-f, while coupling with iodothiophene, iodopyrazole or bromopyridine provided the corresponding 1- (benzyloxy)-5-heteroarylpyrazoles 6a-c.

UR - http://www.scopus.com/inward/record.url?scp=0031774843&partnerID=8YFLogxK

M3 - Journal article

AN - SCOPUS:0031774843

SP - 1604

EP - 1608

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 11

ER -

ID: 45438264