ALKYL AND ARYL ISOTHIOCYANATES AS MASKED PRIMARY AMINES

被引：22
|
作者：
CHO, CG [1 ]
POSNER, GH [1 ]
机构：
[1] JOHNS HOPKINS UNIV,SCH ARTS & SCI,DEPT CHEM,BALTIMORE,MD 21218
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 25期
关键词：
D O I：
10.1016/S0040-4039(00)92512-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Primary and secondary (but not tertiary) alkyl as well as aryl isothiocyanates react rapidly with 4-methyl-1,2-benzenedithiol (1) in methanol at room temperature, releasing the corresponding amines in good yields. This mild and simple procedure for unmasking amines proceeds chemospecifically with isothiocyanates even in the presence of such normally electrophilic and reactive functionalities as carboxylate ester and N-alkylphthalimide.
引用
收藏
页码：3599 / 3602
页数：4
相关论文
共 50 条
  • [1] SYNTHESIS OF PRIMARY ARYL ALKYL AMINES
    MALAVE, TM
    TIRADO, LM
    ORTIZ, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 307 - CHED
  • [2] Kinetics of condensation of aryl isothiocyanates with aryl amines
    Pathrikar, LGY
    Bondge, SP
    Burungale, AS
    Bhingolikar, VE
    Ingle, RD
    Mane, RA
    INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 2002, 41 (12): : 2518 - 2521
  • [3] Enantioselective synthesis of primary aryl alkyl amines.
    Diaz-Espinosa, Y
    Figueroa-Ares, W
    Ortiz, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U614 - U614
  • [4] REACTIONS OF ALKYL AZIDES WITH ARYL ISOTHIOCYANATES
    ABBE, G
    VANLOOCK, E
    VERHELST, G
    TOPPET, S
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (03) : 607 - 608
  • [5] 1-POT SYNTHESIS OF ISOTHIOCYANATES FROM PRIMARY AMINES IN NONAQUEOUS SYSTEM .4. SYNTHESIS OF ALKYL ISOTHIOCYANATES FROM PRIMARY ALKYL AMINES USING DICYANDIAMIDE AS A DEHYDROSULFURIZING AGENT
    YAMAMOTO, T
    TERADA, A
    MURAMATSU, T
    IKEDA, K
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1994, 26 (05) : 555 - 557
  • [6] NEW METHOD FOR PREPARATION OF ALKYL AND ARYL ISOTHIOCYANATES USING AMINES, BUTYLLITHIUM, AND CARBON-DISULFIDE
    SAKAI, S
    AIZAWA, T
    FUJINAMI, T
    JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (13): : 1970 - 1971
  • [7] ANTIMICROBIAL EFFECT OF NEW ARYL, ALKYL ISOTHIOCYANATES
    DROBNICA, L
    NEMEC, P
    ONDREJIC.O
    FOLIA MICROBIOLOGICA, 1970, 15 (03) : 203 - &
  • [8] N-ARYL-N'-ALKYLOXAMIDES FOR THE IDENTIFICATION OF PRIMARY ALKYL AMINES
    RICHARDSON, AG
    PIERCE, JS
    REID, EE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (16) : 4011 - 4012
  • [9] DETERMINATION OF ALKYL THIOUREAS, ISOTHIOCYANATES AND AMINES WITH IODINE MONOCHLORIDE
    VERMA, KK
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) : 2155 - 2156
  • [10] Synthesis and evaluation of alkyl and aryl isothiocyanates as anticancer agents
    Johnson, Amanda L.
    Mays, Jared R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
12345