Novel Synthesis of 5-(Arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles and the Mechanism of Their Formation

Hyunil Lee; Kyongtae Kim; Dongmok Whang; Kimoon Kim

doi:10.1021/jo00100a018

Novel Synthesis of 5-(Arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles and the Mechanism of Their Formation

Hyunil Lee, Kyongtae Kim, Dongmok Whang, Kimoon Kim

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

The reactions of 5-(arylimino)-4-chloro-5H-1,2,3-dithiazoles 1 with excess (6 equiv) bulky dialkylamines such as diethyl-, di-n-propyl-, and di-n-butylamines in CH₂Cl₂ at room temperature gave 5-(arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles 5 in 18-76% yields. Compounds 5 are formed via (arylimino)cyanomethyl alkylamino disulfides 3. Nucleophilic addition of the amines to the carbon atom of the cyano group of 3 and subsequent cyclization afford 5.

Original language	English
Pages (from-to)	6179-6183
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	59
Issue number	21
DOIs	https://doi.org/10.1021/jo00100a018
State	Published - 1 Oct 1994
Externally published	Yes

Access to Document

10.1021/jo00100a018

Cite this

@article{fec01e74aaa44d1ebf46f800d4a60307,

title = "Novel Synthesis of 5-(Arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles and the Mechanism of Their Formation",

abstract = "The reactions of 5-(arylimino)-4-chloro-5H-1,2,3-dithiazoles 1 with excess (6 equiv) bulky dialkylamines such as diethyl-, di-n-propyl-, and di-n-butylamines in CH2Cl2 at room temperature gave 5-(arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles 5 in 18-76\% yields. Compounds 5 are formed via (arylimino)cyanomethyl alkylamino disulfides 3. Nucleophilic addition of the amines to the carbon atom of the cyano group of 3 and subsequent cyclization afford 5.",

author = "Hyunil Lee and Kyongtae Kim and Dongmok Whang and Kimoon Kim",

year = "1994",

month = oct,

day = "1",

doi = "10.1021/jo00100a018",

language = "English",

volume = "59",

pages = "6179--6183",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Novel Synthesis of 5-(Arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles and the Mechanism of Their Formation

AU - Lee, Hyunil

AU - Kim, Kyongtae

AU - Whang, Dongmok

AU - Kim, Kimoon

PY - 1994/10/1

Y1 - 1994/10/1

N2 - The reactions of 5-(arylimino)-4-chloro-5H-1,2,3-dithiazoles 1 with excess (6 equiv) bulky dialkylamines such as diethyl-, di-n-propyl-, and di-n-butylamines in CH2Cl2 at room temperature gave 5-(arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles 5 in 18-76% yields. Compounds 5 are formed via (arylimino)cyanomethyl alkylamino disulfides 3. Nucleophilic addition of the amines to the carbon atom of the cyano group of 3 and subsequent cyclization afford 5.

AB - The reactions of 5-(arylimino)-4-chloro-5H-1,2,3-dithiazoles 1 with excess (6 equiv) bulky dialkylamines such as diethyl-, di-n-propyl-, and di-n-butylamines in CH2Cl2 at room temperature gave 5-(arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles 5 in 18-76% yields. Compounds 5 are formed via (arylimino)cyanomethyl alkylamino disulfides 3. Nucleophilic addition of the amines to the carbon atom of the cyano group of 3 and subsequent cyclization afford 5.

UR - https://www.scopus.com/pages/publications/0028139459

U2 - 10.1021/jo00100a018

DO - 10.1021/jo00100a018

M3 - Article

AN - SCOPUS:0028139459

SN - 0022-3263

VL - 59

SP - 6179

EP - 6183

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

Novel Synthesis of 5-(Arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles and the Mechanism of Their Formation

Abstract

Access to Document

Other files and links

Fingerprint

Cite this