A significantly improved condition for cyclization of phenethylcarbamates to N-alkylated 3,4-dihydroisoquinolones

被引:47
作者
Wang, XJ [1 ]
Tan, J [1 ]
Grozinger, K [1 ]
机构
[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Ridgefield, CT 06877 USA
关键词
D O I
10.1016/S0040-4039(98)01395-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Secondary phenethyl carbamates undergo a Bischler-Napieralski cyclization promoted by phosphorus pentoxide in refluxing phosphorus oxychloride to afford N-alkylated 3,4-dihydroisoquinolones in high yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6609 / 6612
页数:4
相关论文
共 17 条
[1]   A STEREOSELECTIVE FORMAL SYNTHESIS OF (+/-)-(GAMMA)-LYCORANE [J].
ANGLE, SR ;
BOYCE, JP .
TETRAHEDRON LETTERS, 1995, 36 (35) :6185-6188
[2]  
BALAZS L, 1995, SYNTHESIS-STUTTGART, P1373
[3]  
BALAZS L, 1994, SYNTHESIS-STUTTGART, P73
[4]   CONCISE SYNTHETIC ROUTE TO BOTH ENANTIOMERIC FORMS OF 2,3,4,4A-TETRAHYDRO[1,3]DIOXOLO[4,5-J]PHENANTHRIDIN-6(5H)-ONE, THE TETRACYCLIC SKELETON ASSOCIATED WITH THE NARCISSUS ALKALOIDS LYCORICIDINE AND NARCICLASINE [J].
BANWELL, MG ;
COWDEN, CJ ;
MACKAY, MF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) :61-62
[5]   Trifluoromethanesulfonic anhydride-4-(N,N-dimethylamino)pyridine as a reagent combination for effecting Bischler-Napieralski cyclisation under mild conditions: Application to total syntheses of the Amaryllidaceae alkaloids N-methylcrinasiadine, anhydrolycorinone, hippadine and oxoassoanine [J].
Banwell, MG ;
Bissett, BD ;
Busato, S ;
Cowden, CJ ;
Hockless, DCR ;
Holman, JW ;
Read, RW ;
Wu, AW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (24) :2551-2553
[6]   A STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-GAMMA-LYCORANE [J].
BANWELL, MG ;
WU, AW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19) :2671-2672
[7]   CORRELATION OF THE VONBRAUN, RITTER, BISCHLER-NAPIERALSKI, BECKMANN AND SCHMIDT REACTIONS VIA NITRILIUM SALT INTERMEDIATES [J].
FODOR, G ;
NAGUBANDI, S .
TETRAHEDRON, 1980, 36 (10) :1279-1300
[8]   MECHANISM OF BISCHLER-NAPIERALSKI REACTION [J].
FODOR, G ;
PHILLIPS, BA ;
GAL, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (10) :919-&
[9]   PHOTO-REDUCTION OF BENZOPHENONE BY PHTHALIMIDINES AND DIHYDRO-ISOQUINOLONES - STUDY OF CHEMISTRY AND NMR CIDNP [J].
GRAMAIN, JC ;
SIMONET, N ;
VERMEERSCH, G ;
FEBVAYGAROT, N ;
CAPLAIN, S ;
LABLACHECOMBIER, A .
TETRAHEDRON, 1982, 38 (04) :539-550
[10]   STEREOSPECIFIC TOTAL SYNTHESIS OF HEMANTHIDINE AND TAZETTINE [J].
HENDRICKSON, JB ;
BOGARD, TL ;
FISCH, ME ;
GROSSERT, S ;
YOSHIMURA, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7781-7789