A novel hindered macrocyclic tetramine containing two bispidine units. A new type of proton sponge

Yuji Miyahara; Kenta Goto; Takahiko Inazu

doi:10.1016/S0040-4039(01)00341-0

A novel hindered macrocyclic tetramine containing two bispidine units. A new type of proton sponge

Yuji Miyahara, Kenta Goto, Takahiko Inazu

Department of Applied Molecular Chemistry

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

33 Citations (Scopus)

Abstract

A novel cyclam-like macrocyclic tetramine 1a was synthesized via coupling of bispidine and its bis(α-chloroacetamide) followed by reduction. Strongly basic but encrypted nitrogens of 1a were found to abstract a proton from chloroform to form dichlorocarbene.

Original language	English
Pages (from-to)	3097-3099
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(01)00341-0
Publication status	Published - Apr 23 2001

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)00341-0

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title = "A novel hindered macrocyclic tetramine containing two bispidine units. A new type of proton sponge",

abstract = "A novel cyclam-like macrocyclic tetramine 1a was synthesized via coupling of bispidine and its bis(α-chloroacetamide) followed by reduction. Strongly basic but encrypted nitrogens of 1a were found to abstract a proton from chloroform to form dichlorocarbene.",

author = "Yuji Miyahara and Kenta Goto and Takahiko Inazu",

note = "Funding Information: This work was supported in part by a Grant-in-Aid for COE Research {\textquoteleft}Design and Control of Advanced Molecular Assembly Systems{\textquoteright} from the Ministry of Education, Science, Sports and Culture, Japan (#08CE2005).",

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AU - Miyahara, Yuji

AU - Goto, Kenta

AU - Inazu, Takahiko

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for COE Research ‘Design and Control of Advanced Molecular Assembly Systems’ from the Ministry of Education, Science, Sports and Culture, Japan (#08CE2005).

PY - 2001/4/23

Y1 - 2001/4/23

N2 - A novel cyclam-like macrocyclic tetramine 1a was synthesized via coupling of bispidine and its bis(α-chloroacetamide) followed by reduction. Strongly basic but encrypted nitrogens of 1a were found to abstract a proton from chloroform to form dichlorocarbene.

AB - A novel cyclam-like macrocyclic tetramine 1a was synthesized via coupling of bispidine and its bis(α-chloroacetamide) followed by reduction. Strongly basic but encrypted nitrogens of 1a were found to abstract a proton from chloroform to form dichlorocarbene.

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U2 - 10.1016/S0040-4039(01)00341-0

DO - 10.1016/S0040-4039(01)00341-0

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ER -

A novel hindered macrocyclic tetramine containing two bispidine units. A new type of proton sponge

Abstract

All Science Journal Classification (ASJC) codes

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