SYNTHESIS OF A NEW-GENERATION REVERSE-TRANSCRIPTASE INHIBITOR VIA THE BCL3/GACL3-INDUCED CONDENSATION OF ANILINES WITH NITRILES (SUGASAWA REACTION)

被引：24
作者：
HOUPIS, IN
MOLINA, A
DOUGLAS, AW
XAVIER, L
LYNCH, J
VOLANTE, RP
REIDER, PJ
机构：
[1] Merck Research Laboratories, Process Research, Rahway, NJ 07065, P.O. Box 2000
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 37期
关键词：
D O I：
10.1016/0040-4039(94)85011-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of 1 was achieved in high overall yield through a mechanism-based improvement of the preparation of o-acyl anilines.
引用
收藏
页码：6811 / 6814
页数：4
相关论文
共 18 条
[1]  
ARCHER GA, 1968, CHEM REV, P755
[2]  
DOUGLAS AW, TETRAHEDRON LETT
[3]   THE EFFICACY OF AZIDOTHYMIDINE (AZT) IN THE TREATMENT OF PATIENTS WITH AIDS AND AIDS-RELATED COMPLEX - A DOUBLE-BLIND, PLACEBO-CONTROLLED TRIAL [J].
FISCHL, MA ;
RICHMAN, DD ;
GRIECO, MH ;
GOTTLIEB, MS ;
VOLBERDING, PA ;
LASKIN, OL ;
LEEDOM, JM ;
GROOPMAN, JE ;
MILDVAN, D ;
SCHOOLEY, RT ;
JACKSON, GG ;
DURACK, DT ;
KING, D .
NEW ENGLAND JOURNAL OF MEDICINE, 1987, 317 (04) :185-191
[4]   ORTHO FUNCTIONALIZATION OF AROMATIC-AMINES - ORTHO LITHIATION OF N-PIVALOYLANILINES [J].
FUHRER, W ;
GSCHWEND, HW .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (07) :1133-1136
[5]  
HARADA T, 1991, SYNTHESIS-STUTTGART, P1216
[6]   2',3'-DIDEOXYINOSINE (DDI) IN PATIENTS WITH THE ACQUIRED-IMMUNODEFICIENCY-SYNDROME OR AIDS-RELATED COMPLEX - A PHASE-I TRIAL [J].
LAMBERT, JS ;
SEIDLIN, M ;
REICHMAN, RC ;
PLANK, CS ;
LAVERTY, M ;
MORSE, GD ;
KNUPP, C ;
MCLAREN, C ;
PETTINELLI, C ;
VALENTINE, FT ;
DOLIN, R .
NEW ENGLAND JOURNAL OF MEDICINE, 1990, 322 (19) :1333-1340
[7]   MOLECULAR TARGETS FOR AIDS THERAPY [J].
MITSUYA, H ;
YARCHOAN, R ;
BRODER, S .
SCIENCE, 1990, 249 (4976) :1533-1544
[8]   ORTHO FUNCTIONALIZATION OF N-(TERT-BUTOXYCARBONYL)ANILINE [J].
MUCHOWSKI, JM ;
VENUTI, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4798-4801
[9]   THE CATALYTIC FRIEDEL-CRAFTS ACYLATION REACTION USING A CATALYST GENERATED FROM GACL3 AND A SILVER SALT [J].
MUKAIYAMA, T ;
OHNO, T ;
NISHIMURA, T ;
SUDA, S ;
KOBAYASHI, S .
CHEMISTRY LETTERS, 1991, (06) :1059-1062
[10]   THE TOXICITY OF AZIDOTHYMIDINE (AZT) IN THE TREATMENT OF PATIENTS WITH AIDS AND AIDS-RELATED COMPLEX - A DOUBLE-BLIND, PLACEBO-CONTROLLED TRIAL [J].
RICHMAN, DD ;
FISCHL, MA ;
GRIECO, MH ;
GOTTLIEB, MS ;
VOLBERDING, PA ;
LASKIN, OL ;
LEEDOM, JM ;
GROOPMAN, JE ;
MILDVAN, D ;
HIRSCH, MS ;
JACKSON, GG ;
DURACK, DT ;
NUSINOFFLEHRMAN, S .
NEW ENGLAND JOURNAL OF MEDICINE, 1987, 317 (04) :192-197
12