Direct microwave synthesis of N,N′-diacylhydrazines and boc-protected hydrazides by in situ carbonylations under air

被引：33

作者：

Herrero, MA ^{[1
]}

Wannberg, J ^{[1
]}

Larhed, M ^{[1
]}

机构：

[1] Univ Uppsala, Dept Med Chem, S-75123 Uppsala, Sweden

来源：

SYNLETT | 2004年 / 13期

关键词：

microwave; carbonylation; molybdenum hexacarbonyl; hydrazide; fluorous;

D O I：

10.1055/s-2004-832837

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed hydrazidocarbonylations of aryl iodides and bromides were performed by controlled microwave irradiation, employing Mo(CO)(6) as a convenient CO source. A fluorous phosphine ligand was succesfully used to recycle the catalytic system. Finally, dehydration of a diacylhydrazine to the corresponding 1,3,4-oxadiazole was achieved with POCl3 in a one-pot procedure.

引用

页码：2335 / 2338

页数：4

共 50 条

[41] ORGN 551-Palladium-catalyzed oxidation of Boc-protected N-methylamines with IOAc as the oxidant: A Boc-directed sp3 C-H bond activation
Wang, Donghui
Hao, Xueshi
Yu, Jin-Quan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
[42] Practical one-pot amidation of N-Alloc-, N-Boc-, and N-Cbz protected amines under mild conditions
Hong, Wan Pyo
Van Hieu Tran
Kim, Hee-Kwon
RSC ADVANCES, 2021, 11 (26) : 15890 - 15895
[43] Regioselective One-pot Synthesis of N-Fmoc/Cbz, N''-Boc Protected Indol-(3)-ylmethylhydrazines
Vahter, Kati
Mastitski, Anton
Haljasorg, Toiv
Jarv, Jaak
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2020, 52 (03) : 212 - 218
[44] Chemistry of N-boc-N-tert-butylthiomethyl-protected α-aminoorganostannanes:: Diastereoselective synthesis of primary β-amino alcohols from α-aminoorganostannanes
Ncube, A
Park, SB
Chong, JM
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11): : 3625 - 3636
[45] A general method for preparation of N-Boc-protected or N-Fmoc-protected ,-didehydropeptide building blocks and their use in the solid-phase peptide synthesis
Wolczanski, Grzegorz
Lisowski, Marek
JOURNAL OF PEPTIDE SCIENCE, 2018, 24 (8-9)
[46] A convenient synthesis of N-Boc-protected tert-butyl esters of phenylglycines from benzylamines
Kise, N
Ozaki, H
Terui, H
Ohya, K
Ueda, N
TETRAHEDRON LETTERS, 2001, 42 (43) : 7637 - 7639
[47] FACILE AND EFFICIENT N-BOC DEPROTECTION OF AMIDE AND SULFONAMIDE UNDER MICROWAVE IRRADIATION IN WATER
Huang, Zhi-you
Li, Wen-sheng
Xu, Jia
Xiang, Bing-rong
Li, Min-xin
Chen, Li -jun
Wang, Ye-she
HETEROCYCLES, 2022, 104 (09) : 1559 - 1564
[48] Diastereoselective synthesis of protected 4-epi-vancosamine from (S)-N-Boc-N,O-isopropylidene-α-methylserinal
Avenoza, A
Busto, JH
Corzana, F
Peregrina, JM
Sucunza, D
Zurbano, MM
TETRAHEDRON-ASYMMETRY, 2003, 14 (08) : 1037 - 1043
[49] An improved synthesis of (S)- or (R)-N-boc-protected 1,5-benzothiazepine derivatives
Amblard, M
Calmès, M
Roques, V
Tabet, S
Loffet, A
Martinez, J
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2002, 34 (04) : 405 - 415
[50] Synthesis of N-Boc Protected Hydrazine Diacids as Key Structural Units for the Formation of α-Helix Mimics
Anderson, Laura
Topper, Melissa
Jain, Priyesh
McIntosh, Emily
McLaughlin, Mark L.
PEPTIDES FOR YOUTH, 2009, 611 : 211 - 212

← 1 2 3 4 5 →