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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 19
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Original Articles

NUCLEOPHILIC ADDITION TO 1,2-DIMETHYL-3-ARYLSULFONYL- 4,5-DIHYDROIMIDAZOLIUM IODIDES

Chizhong Xia Institute of Molecular Science, Shanxi University, Taiyuan, 030006, China
,
Jianxin Chen Institute of Molecular Science, Shanxi University, Taiyuan, 030006, China
,
Hongxing Wang Institute of Molecular Science, Shanxi University, Taiyuan, 030006, China
,
Congmin Kang Institute of Molecular Science, Shanxi University, Taiyuan, 030006, China
,
Bingjun Zhao Institute of Molecular Science, Shanxi University, Taiyuan, 030006, China
,
Yanping Ni Institute of Molecular Science, Shanxi University, Taiyuan, 030006, China
&
Peiwen Zhou Prolinx, Inc., 22322 20th Ave. SE, Bothell, WA, 98021, U.S.A.Correspondence[email protected]
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Pages 2979-2984 | Received 18 Sep 2001, Published online: 16 Aug 2006
 
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ABSTRACT

Benzenesulfonamide derivatives 6–11 were prepared from the reactions of arylsulfonylimidazolium iodides 1–5 with malononitrile or nitromethane anions in high yield. The addition product 11 reacted further with tryptamine to produce 2,3,4,9-tetrahydro-1-methyl-1-nitromethyl-1H-pyrido[3,4]indole (12) in excellent yield through Pictet–Spengler type reaction.

ACKNOWLEDGMENT

This work was supported by the National Natural Science Foundation of China, and the Natural Science Foundation of Shanxi Province, China.

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