Synthesis of conformationally restricted nicotine analogues by intramolecular [3+2] cycloaddition

Xiaobao Yang; Shengjun Luo; Fang Fang; Peng Liu; Yong Lu; Mingyuan He; Hongbin Zhai

doi:10.1016/j.tet.2005.12.032

Synthesis of conformationally restricted nicotine analogues by intramolecular [3+2] cycloaddition

Xiaobao Yang, Shengjun Luo, Fang Fang, Peng Liu, Yong Lu, Mingyuan He, Hongbin Zhai

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

19 Scopus citations

Abstract

We describe the synthesis of a series of conformationally constrained nicotine analogues 2-5 from appropriate pyridine-containing enals, featuring an intramolecular azomethine ylide-alkene [3+2] cycloaddition. The objective of the current project is to develop new selective nAChRs-targeting ligands. Of the nicotine analogues that we have studied, the conformation-restricting ring B unit can be either a five-membered carbocycle, or a six-membered carbocycle or heterocycle. The present work constitutes a general method for rapid assembly of other related tricyclic nicotine analogues.

Original language	English
Pages (from-to)	2240-2246
Number of pages	7
Journal	Tetrahedron
Volume	62
Issue number	10
DOIs	https://doi.org/10.1016/j.tet.2005.12.032
State	Published - 6 Mar 2006
Externally published	Yes

Keywords

Conformationally restricted
Intramolecular [3+2] cycloaddition
Nicotine analogues
Synthesis

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10.1016/j.tet.2005.12.032

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title = "Synthesis of conformationally restricted nicotine analogues by intramolecular [3+2] cycloaddition",

abstract = "We describe the synthesis of a series of conformationally constrained nicotine analogues 2-5 from appropriate pyridine-containing enals, featuring an intramolecular azomethine ylide-alkene [3+2] cycloaddition. The objective of the current project is to develop new selective nAChRs-targeting ligands. Of the nicotine analogues that we have studied, the conformation-restricting ring B unit can be either a five-membered carbocycle, or a six-membered carbocycle or heterocycle. The present work constitutes a general method for rapid assembly of other related tricyclic nicotine analogues.",

keywords = "Conformationally restricted, Intramolecular [3+2] cycloaddition, Nicotine analogues, Synthesis",

author = "Xiaobao Yang and Shengjun Luo and Fang Fang and Peng Liu and Yong Lu and Mingyuan He and Hongbin Zhai",

note = "Funding Information: We thank NSFC (No. 20372073), STCSM ({\textquoteleft}Post-Venus{\textquoteright} Program, No. 05QMH1416), GCCP of ECNU, and Ministry of Human Resources of PRC for financial support.",

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doi = "10.1016/j.tet.2005.12.032",

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journal = "Tetrahedron",

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TY - JOUR

T1 - Synthesis of conformationally restricted nicotine analogues by intramolecular [3+2] cycloaddition

AU - Yang, Xiaobao

AU - Luo, Shengjun

AU - Fang, Fang

AU - Liu, Peng

AU - Lu, Yong

AU - He, Mingyuan

AU - Zhai, Hongbin

N1 - Funding Information: We thank NSFC (No. 20372073), STCSM (‘Post-Venus’ Program, No. 05QMH1416), GCCP of ECNU, and Ministry of Human Resources of PRC for financial support.

PY - 2006/3/6

Y1 - 2006/3/6

N2 - We describe the synthesis of a series of conformationally constrained nicotine analogues 2-5 from appropriate pyridine-containing enals, featuring an intramolecular azomethine ylide-alkene [3+2] cycloaddition. The objective of the current project is to develop new selective nAChRs-targeting ligands. Of the nicotine analogues that we have studied, the conformation-restricting ring B unit can be either a five-membered carbocycle, or a six-membered carbocycle or heterocycle. The present work constitutes a general method for rapid assembly of other related tricyclic nicotine analogues.

AB - We describe the synthesis of a series of conformationally constrained nicotine analogues 2-5 from appropriate pyridine-containing enals, featuring an intramolecular azomethine ylide-alkene [3+2] cycloaddition. The objective of the current project is to develop new selective nAChRs-targeting ligands. Of the nicotine analogues that we have studied, the conformation-restricting ring B unit can be either a five-membered carbocycle, or a six-membered carbocycle or heterocycle. The present work constitutes a general method for rapid assembly of other related tricyclic nicotine analogues.

KW - Conformationally restricted

KW - Intramolecular [3+2] cycloaddition

KW - Nicotine analogues

KW - Synthesis

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U2 - 10.1016/j.tet.2005.12.032

DO - 10.1016/j.tet.2005.12.032

M3 - Article

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EP - 2246

JO - Tetrahedron

JF - Tetrahedron

IS - 10

ER -

Synthesis of conformationally restricted nicotine analogues by intramolecular [3+2] cycloaddition

Abstract

Keywords

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