Selective synthesis of 2,3-disubstituted-2H-isoindol-1-ylphosphonate and 2,3-disubstituted-1,2-dihydroiso-quinolin-1-ylphosphonate via metal-tuned reaction of α-amino (2-alkynylphenyl)methylphosphonate

被引：99

作者：

Ding, Qiuping

Ye, Yang

Fan, Renhua

Wu, Jie

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 14期

关键词：

D O I：

10.1021/jo070716d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium(II)-catalyzed reaction of alpha-amino (2-alkynylphenyl)methylphosphonate provides a novel and efficient route to 2,3-disubstituted-2H-isoindol-1-ylphosphonate via 5-exo-cyclization and [1,5]-H shift; while 2,3-disubstituted-1,2-dihydroisoquinolin-1-ylphosphonate is afforded through 6-endo-cyclization utilizing silver triflate as catalyst.

引用

页码：5439 / 5442

页数：4

共 60 条

[1] PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS
ALLEN, JG
ATHERTON, FR
HALL, MJ
HASSALL, CH
HOLMES, SW
LAMBERT, RW
NISBET, LJ
RINGROSE, PS
[J]. NATURE, 1978, 272 (5648) : 56 - 58
[2] Catalytic and selective conversion of (Z)-2-en-4-ynoic acids to either 2H-pyran-2-ones in the presence of ZnBr2 or (Z)-5-alkylidenefuran-2(5H)-ones in the presence of Ag2CO3
Anastasia, L
Xu, C
Negishi, E
[J]. TETRAHEDRON LETTERS, 2002, 43 (32) : 5673 - 5676
[3] PALLADIUM-CATALYZED COUPLING OF ARYL AND VINYL TRIFLATES OR HALIDES WITH 2-ETHYNYLANILINE - AN EFFICIENT ROUTE TO FUNCTIONALIZED 2-SUBSTITUTED INDOLES
ARCADI, A
CACCHI, S
MARINELLI, F
[J]. TETRAHEDRON LETTERS, 1989, 30 (19) : 2581 - 2584
[4] Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines
Asao, N
Yudha, S
Nogami, T
Yamamoto, Y
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) : 5526 - 5528
[5] Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction
Aschwanden, P
Frantz, DE
Carreira, EM
[J]. ORGANIC LETTERS, 2000, 2 (15) : 2331 - 2333
[6] Synthesis of 2-arylbenzo[b]furans via copper(I)-catalyzed coupling of o-iodophenols and aryl acetylenes
Bates, CG
Saejueng, P
Murphy, JM
Venkataraman, D
[J]. ORGANIC LETTERS, 2002, 4 (26) : 4727 - 4729
[7] Phosphatase inhibitors .3. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase
Beers, SA
Schwender, CF
Loughney, DA
Malloy, E
Demarest, K
Jordan, J
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (10) : 1693 - 1701
[8] Regioselective synthesis of natural and unnatural (Z)-3-(1-alkylidene)phthalides and 3-substituted isocoumarins starting from methyl 2-hydroxybenzoates
Bellina, F
Ciucci, D
Vergamini, P
Rossi, R
[J]. TETRAHEDRON, 2000, 56 (16) : 2533 - 2545
[9] BLACK TH, 1995, ENCY REAGENTS ORGANI, V6, P4476
[10] PALLADIUM-CATALYZED CYCLIZATION OF 2-ALKYNYLANILINES TO 2-SUBSTITUTED INDOLES UNDER AN ACIDIC 2-PHASE SYSTEM
CACCHI, S
CARNICELLI, V
MARINELLI, F
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 475 (1-2) : 289 - 296

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