An easy access to aryl azides from aryl amines under neutral conditions

被引：55

作者：

Das, J ^{[1
]}

Patil, SN ^{[1
]}

Awasthi, R ^{[1
]}

Narasimhulu, CP ^{[1
]}

Trehan, S ^{[1
]}

机构：

[1] Dr Reddys Labs Ltd, Discovery Res, Hyderabad 500049, Andhra Pradesh, India

来源：

SYNTHESIS-STUTTGART | 2005年 / 11期

关键词：

amines; azides; anilines; diazo compounds; sodium azide;

D O I：

10.1055/s-2005-869974

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of substituted aryl amines were transformed into aryl azides using t-BuONO and moist NaN3 in t-BuOH in good to excellent yields. Smooth transformation was observed with anilines, having electron withdrawing and donating groups. Both acid- and base-sensitive groups survived the reaction conditions.

引用

页码：1801 / 1806

页数：6

共 50 条

[41] Synthesis of aryl azides from aryl halides promoted by Cu2O/tetraethylammonium prolinate
Hajipour, Abdol R.
Mohammadsaleh, Fatemeh
TETRAHEDRON LETTERS, 2014, 55 (50) : 6799 - 6802
[42] Aluminum-catalyzed efficient synthesis of anilides by the acylation of aryl amines under ultrasonic conditions
Reddy, Muthukur Bhojegowd Madhusudana
Jayashankara, Vaderapura Puttaramegowda
Pasha, Mohamed Afzal
GREEN CHEMISTRY LETTERS AND REVIEWS, 2013, 6 (01) : 107 - 112
[43] An improved synthesis of pyrazolines from aryl azides and acrylic esters
Yadav, JS
Reddy, BVS
Geetha, V
SYNLETT, 2002, (03) : 513 - 515
[44] A One-Pot Method for the Iodination of Aryl Amines via Stable Aryl Diazonium Silica Sulfates Under Solvent-Free Conditions
Zarei, Amin
Hajipour, Abdol R.
Khazdooz, Leila
SYNTHESIS-STUTTGART, 2009, (06): : 941 - 944
[45] Synthesis of Indolines, Indoles, and Benzopyrrolizidinones from Simple Aryl Azides
Brucelle, Francois
Renaud, Philippe
ORGANIC LETTERS, 2012, 14 (12) : 3048 - 3051
[46] Reductive dimerization of azides to secondary amines under hydrogenation conditions
An, IH
Seong, HR
Ahn, KH
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2004, 25 (03): : 420 - 422
[47] Synthesis of Aryl Trimethylstannanes from Aryl Amines: A Sandmeyer-Type Stannylation Reaction
Qiu, Di
Meng, He
Jin, Liang
Wang, Shuai
Tang, Shengbo
Wang, Xi
Mo, Fanyang
Zhang, Yan
Wang, Jianbo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) : 11581 - 11584
[48] COPPER BIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATE)-CATALYZED COUPLING OF SODIUM AZIDE WITH ARYL IODIDES/BORONIC ACIDS TO ARYL AZIDES OR ARYL AMINES
Lanke, Satish R.
Bhanage, Bhalchandra M.
SYNTHETIC COMMUNICATIONS, 2014, 44 (03) : 399 - 407
[49] Generation of benzyne from aryl benziodoxaborole triflate under aqueous conditions and its reactions with alkyl aryl sulfides
Yoshimura, Akira
Ngo, Kim
Mironova, Irina A.
Gardner, Zachary S.
Ogura, Nami
Ueki, Akiharu
Yusubov, Mekhman S.
Saito, Akio
Zhdankin, Viktor V.
ARKIVOC, 2024,
[50] Selective deprotection of aryl acetates, benzoates, pivalates, and tosylates under nonhydrolytic and virtually neutral conditions
Chakraborti, AK
Nayak, MK
Sharma, L
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21): : 8027 - 8030

← 1 2 3 4 5 →