公开(公告)号：WO1996023770A1

公开(公告)日：1996-08-08

申请号：PCT/US1996000991

申请日：1996-01-25

Applicant: CATALYTICA, INC.

Inventor： CATALYTICA, INC. ,  GRUBER, John, M. ,  BULLS, Ray, A.

IPC: C07D209/34

CPC classification number: C07D209/34 ,  C07C201/12 ,  C07C253/30 ,  C07C205/56 ,  C07C255/41

Abstract: The present invention provides processes having practical utility for preparing 2-oxindoles, N-hydroxy-2-oxindoles, or mixtures thereof comprising: catalytically hydrogenating a 2-nitroarylmalonate diester to produce a 2-(N-hydroxyamino)arylmalonate diester, a 2-aminoarylmalonate diester, or mixtures thereof as a first reaction intermediate: cyclizing, by intramolecular aminolysis of one ester group, the first reaction intermediate to produce a N-hydroxy-2-oxindole-3-carboxylate ester, 2-oxindole-3-carboxylate ester, or mixtures thereof as a second reaction intermediate; and hydrolyzing and decarboxylating the remaining ester group of the second reaction intermediate to produce the N-hydroxy-2-oxindole, the 2-oxindole, or mixtures thereof, wherein the cyclization reaction and the hydrolysis and decarboxylation reaction are conducted in situ with the catalytic hydrogenation reaction without isolation of said reaction intermediates.

Abstract translation: 本发明提供了用于制备2-羟基吲哚，N-羟基-2-羟基吲哚或其混合物的实际应用的方法，其包括：催化氢化2-硝基芳基丙二酸二酯以产生2-（N-羟基氨基）芳基丙二酸二酯，2- 氨基芳基丙二酸二酯或其混合物作为第一反应中间体：通过一个酯基团的分子内氨基化来环化第一反应中间体以产生N-羟基-2-羟基吲哚-3-羧酸酯，2-羟基吲哚-3-羧酸酯 ，或其混合物作为第二反应中间体; 并将第二反应中间体的剩余酯基水解和脱羧以产生N-羟基-2-羟基吲哚，2-羟基吲哚或其混合物，其中环化反应和水解和脱羧反应与催化剂原位进行 不分离所述反应中间体的氢化反应。

公开(公告)号：WO1995020574A1

公开(公告)日：1995-08-03

申请号：PCT/US1995001005

申请日：1995-01-27

Applicant: CATALYTICA, INC.

Inventor： CATALYTICA, INC. ,  GRUBER, John, M.

IPC: C07D209/32

CPC classification number: C07D223/10 ,  C07C273/1818 ,  C07D209/34 ,  C07C275/54

Abstract: The present invention provides a process for preparing 2-oxindole-1-carboxamides, comprising reacting N-acyl 2-oxindole-1-carboxamides with alcohols in the presence of aprotic weak Lewis acid catalysts. In certain processes of the present invention a 2-oxindole-1-carboxamide is prepared from a 2-oxindole by reacting the 2-oxindole with an acyl isocyanate to produce the N-acyl 2-oxindole-1-carboxamide as an intermediate, which is then reacted with alcohol in the presence of aprotic weak Lewis acid catalysts. The N-acyl 2-oxindole-1-carboxamide intermediate may be converted to the 2-oxindole-1-carboxamide without isolation.

Abstract translation: 本发明提供2-羟基吲哚-1-甲酰胺的制备方法，其包括在非质子弱路易斯酸催化剂存在下使N-酰基2-羟基吲哚-1-甲酰胺与醇反应。 在本发明的某些方法中，2-羟基吲哚-1-甲酰胺由2-羟基吲哚通过使2-羟基吲哚与酰基异氰酸酯反应制备N-酰基-2-羟基吲哚-1-甲酰胺作为中间体，其中 然后在非质子弱路易斯酸催化剂存在下与醇反应。 N-酰基2-羟基吲哚-1-甲酰胺中间体可以不分离地转化成2-羟基吲哚-1-甲酰胺。

公开(公告)号：EP0741702A1

公开(公告)日：1996-11-13

申请号：EP95908677.0

申请日：1995-01-27

Applicant: CATALYTICA, INC.

Inventor： GRUBER, John, M.

IPC: C07C273 ,  C07D209 ,  C07D223 ,  C07C275

CPC classification number: C07D223/10 ,  C07C273/1818 ,  C07D209/34 ,  C07C275/54

Abstract: The present invention provides a process for preparing 2-oxindole-1-carboxamides, comprising reacting N-acyl 2-oxindole-1-carboxamides with alcohols in the presence of aprotic weak Lewis acid catalysts. In certain processes of the present invention a 2-oxindole-1-carboxamide is prepared from a 2-oxindole by reacting the 2-oxindole with an acyl isocyanate to produce the N-acyl 2-oxindole-1-carboxamide as an intermediate, which is then reacted with alcohol in the presence of aprotic weak Lewis acid catalysts. The N-acyl 2-oxindole-1-carboxamide intermediate may be converted to the 2-oxindole-1-carboxamide without isolation.