A new method of synthesizing deoxybenzoins from 1,3-dimethyl-2-(α- benzyloxybenzyl)imidazolium and 1,3-dimethyl-2-(α- benzyloxybenzyl)benzimidazolium iodides based on Wittig-type rearrangement

DOI: 10.1248/cpb.45.1235

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1235 - 1242 (1997)

Update date:2022-08-03

Topics:

Authors:

Miyashita, Akira

Matsuoka, Yoshiyuki

Suzuki, Yumiko

Iwamoto, Ken-Ichi

Higashino, Takeo

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1248/cpb.45.1235

The treatment of 1,3-dimethyl-2-(α-benzyloxybenzyl)benzimidazolium iodides 1 with a base gave deoxybenzoins 2 in moderate yields. Sodium hydride (NaH), potassium carbonate (K₂CO₃), and cesium carbonate (Cs₂CO₃) were effective bases in this reaction. Deoxybenzoins 2 were produced through rearrangement of the benzyl group followed by expulsion of the 1,3- dimethylbenzimidazolium ylide (A). The rearrangement proceeds in a way similar to Wittig rearrangement. Deoxybenzoins 2 were also formed in good yields from 1,3-dimethyl-2-(α-benzyloxybenzyl)imidazolium iodides 4 upon similar treatment. However, the quaternary salts having a thiazolium moiety 5a and a pyridinium moiety 6a failed to produce deoxybenzoin (2a).

Full text of DOI:10.1248/cpb.45.1235

NII-Electronic Library Service

Products guided by the article

Product name:1-(1-Methyl-1H-benzoimidazol-2-yl)-1,2-diphenyl-ethanol

Cas No:187336-09-0

R&D Labs maybe for 187336-09-0

Hangzhou Ocean Chemical Co., Ltd.

website:http://www.hzoceanchem.com

Contact:+86-571-88025872, 28272092, 28272096

Address:Room 623 ,Building No 1 , COFCO Radius Commercial Center Xiwen Road, Xiacheng District, Hangzhou, Zhejiang Province, China
Jai Radhe Sales

website:http://www.jairadhesales.com

Contact:0091-79-26431096

Address:309 Harikrupa Tower,Nr old Sharda Mandir Char Rasta,Ellisbridge
Shanghai Dano Pharmaceutical Co.,Ld.(expird)

Contact:+86-592-6266840

Address:Building 1 Room 512, 720 Cailun Rd, Zhangjiang High-Tech Park, Shanghai 201203, China
Zhejiang Kaili Industrial Co., Ltd

Contact:+86-571-85241926

Address:lantian business center,No.18 Moganshan Road
Beijing Ribio Biotech Co.,Ltd

Contact:86-10-62664360

Address:Building 10,No.18 AnNingZhuang East Road, GuangHua Pioneer Park,HaiDian District, BeiJing China

Relevant to this article

Synthesis, in vitro anti-HIV activity, and biological stability of 5'- O-myristoyl analogue derivatives of 3'-fluoro-2',3'dideoxythymidine (FLT) as potential bifunctional prodrugs of FLT

Doi:10.1080/07328319808004216
(1998)
B,B-dihaloalkylboranes as efficient reagents for the stereoselective synthesis of Syn-aldols

Doi:10.1016/S0040-4039(96)02448-3
(1997)
'meso-Selective' functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation

Doi:10.1016/S0040-4039(02)00154-5
(2002)
Efficient preparation of the 18-methoxycoronaridine side-chain precursor

Doi:10.1055/s-2006-942489
(2006)
Design and syntheses of potent and selective dipeptide inhibitors of Candida albicans myristoyl-CoA:protein N-myristoyltransferase

Doi:10.1021/jm00011a001
(1995)
Design and synthesis of hapten to induce phospholipase A₂-like catalytic antibody

Doi:10.1016/S0960-894X(97)00018-8
(1997)

Article Doi