Catalytic carbonylation of 3-bromomethyl-5,6-dihydro-4H-1,2-oxazines:: General approach to the synthesis of 3-methoxycarbonylmethyl-5,6-dihydro-4H-1,2-oxazines from available precursors

被引：11

作者：

Eliseev, Oleg L. ^{[1
]}

Ivashkin, Pavel E. ^{[1
]}

Ostapenko, Aduard G. ^{[1
]}

Lesiv, Alexey V. ^{[1
]}

Khomutova, Yulia A. ^{[1
]}

Ioffe, Sema L. ^{[1
]}

Lapidus, Albert L. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

来源：

SYNLETT | 2006年 / 14期

关键词：

1,2-oxazines; carbonylations; palladium;

D O I：

10.1055/s-2006-949616

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach to the stereoselective synthesis of previously unknown 5,6-dihydro-4H-1,2-oxazine-3-yl acetates by catalytic carbonylation of available 3-bromomethyl-5,6-dihydro-4H-1,2-oxazines is elaborated.

引用

页码：2239 / 2240

页数：2

共 50 条

[1] REARRANGEMENT OF CYCLOPROPYL KETONE OXIMES TO 5,6-DIHYDRO-4H-1,2-OXAZINES
RENTZEA, CN
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (03): : 199 - 199
[2] A convenient procedure for the synthesis of substituted 3-α-haloalkyl-5,6-dihydro-4H-1,2-oxazines
Klenov, MS
Lesiv, AV
Khomutova, YA
Nesterov, ID
Ioffe, SL
SYNTHESIS-STUTTGART, 2004, (08): : 1159 - 1170
[3] A convenient procedure for the synthesis of 3-substituted 5,6-dihydro-4H-1,2-oxazines from nitroethane
Sukhorukov, Alexey Yu.
Klenov, Michael S.
Ivashkin, Pavel E.
Lesiv, Alexey V.
Khomutova, Yulya A.
Ioffe, Sema L.
SYNTHESIS-STUTTGART, 2007, (01): : 97 - 107
[4] THERMAL AND ACID-CATALYZED REARRANGEMENTS OF 5,6-DIHYDRO-4H-1,2-OXAZINES
FARAGHER, R
GILCHRIST, TL
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (01): : 258 - 262
[5] Stereoselective preparation of 4,5-dihydroxy-5,6-dihydro-4H-1,2-oxazines and their derivatives
Zimmer, R
Homann, K
Angermann, J
Reissig, HU
SYNTHESIS-STUTTGART, 1999, (07): : 1223 - 1235
[6] HIGHLY DIASTEREOSELECTIVE DEPROTONATION AND SUBSTITUTION OF CHIRAL 5,6-DIHYDRO-4H-1,2-OXAZINES
HIPPELI, C
REISSIG, HU
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16): : 3884 - 3886
[7] AN EFFICIENT AND SIMPLE SYNTHESIS OF 3,4,5,6-TETRAHYDRO-2H-1,2-OXAZINES BY SODIUM CYANOBOROHYDRIDE REDUCTION OF 5,6-DIHYDRO-4H-1,2-OXAZINES
ZIMMER, R
ARNOLD, T
HOMANN, K
REISSIG, HU
SYNTHESIS-STUTTGART, 1994, (10): : 1050 - 1056
[8] REACTIONS OF 6-[BIS(TRIMETHYLSILYL)AMINO]-5,6-DIHYDRO-4H-1,2-OXAZINES
PAULINI, K
GEROLD, A
REISSIG, HU
LIEBIGS ANNALEN, 1995, (04): : 667 - 671
[9] Rearrangement of 3-alkylidene-2-siloxy-tetrahydro-1,2-oxazines (ASENA). A new approach toward the synthesis of 3-α-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines
Tabolin, Andrey A.
Lesiv, Alexey V.
Khomutova, Yulia A.
Nelyubina, Yulia V.
Ioffe, Sema L.
TETRAHEDRON, 2009, 65 (23) : 4578 - 4592
[10] Catalytic hydrogenation of 5,6-dihydro-4H-1,2-oxazines bearing a functionalized methylene group at C-3
Sukhorukov, Alexey Yu.
Lesiv, Alexey V.
Eliseev, Oleg L.
Khomutova, Yulia A.
Ioffe, Sema L.
Borissova, Alexandra O.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (23) : 4025 - 4034

← 1 2 3 4 5 →