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 24 条

[1] Barthel-Rosa LP, 1999, COORDIN CHEM REV, V190, P587
[2] Synthesis of 1,3,4-oxadiazoles using polymer-supported reagents
Brain, CT
Brunton, SA
[J]. SYNLETT, 2001, (03) : 382 - 384
[3] A soluble fluorous palladium complex that promotes heck reactions and can be recovered and reused
Curran, DP
Fischer, K
Moura-Letts, G
[J]. SYNLETT, 2004, (08) : 1379 - 1382
[4] Curran DP, 1998, ANGEW CHEM INT EDIT, V37, P1175, DOI 10.1002/(SICI)1521-3773(19980518)37:9<1174::AID-ANIE1174>3.0.CO
[5] 2-P
[6] Fluorous phase separation techniques in catalysis
de Wolf, E
van Koten, G
Deelman, BJ
[J]. CHEMICAL SOCIETY REVIEWS, 1999, 28 (01) : 37 - 41
[7] Comprehensive survey of combinatorial library synthesis: 2002
Dolle, RE
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (06): : 693 - 753
[8] Rapid palladium-catalyzed synthesis of esters from aryl halides utilizing Mo(CO)6 as a solid carbon monoxide source
Georgsson, J
Hallberg, A
Larhed, M
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (04): : 350 - 352
[9] Application of palladacycles in Heck type reactions
Herrmann, WA
Böhm, VPW
Reisinger, CP
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 23 - 41
[10] Design and synthesis of pseudo-symmetric HIV protease inhibitors containing a novel hydroxymethylcarbonyl (HMC)-hydrazide isostere
Hidaka, K
Kimura, T
Hayashi, Y
McDaniel, KF
Dekhtyar, T
Colletti, L
Kiso, Y
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (01) : 93 - 96

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