Multiple Diamine-Dialdehyde Condensations. Synthesis of Heterocyclic Dodecalenes

Mordecai Rabinovitz; Israel Agranat; Wu Chang Shaw

doi:10.1021/jo00328a005

Multiple Diamine-Dialdehyde Condensations. Synthesis of Heterocyclic Dodecalenes

Mordecai Rabinovitz
, Israel Agranat
, Wu Chang Shaw

Institute of Chemistry

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

2 Scopus citations

Abstract

The diamine-dialdehyde condensation of biphenyl-2,6,2',6'-tetracarbaldehyde (6) and 2,2'-diaminobiphenyl (3) in benzene (TsOH catalyst) gave the tetra Schiff base 9,15,24,30-tetraazahexabenzo[d,f,jk,o,q,uv] dodecalene (4). 10,14,25,29-Tetraaza[d,f,jk,o,q,uv]dodecalene (5) was prepared analogously from 2,6,2',6,-tetraaminobiphenyl (7) and biphenyl-2,2'-dicarbaldehyde (2). The condensation of 6 with o-phenylenediamine and with 2,3-diaminonaphthalene afforded “hydride shift” products 10 and 13. The geometries of 4 and 5 are briefly discussed.

Original language	English
Pages (from-to)	3018-3020
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	46
Issue number	15
DOIs	https://doi.org/10.1021/jo00328a005
State	Published - Jul 1981

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title = "Multiple Diamine-Dialdehyde Condensations. Synthesis of Heterocyclic Dodecalenes",

abstract = "The diamine-dialdehyde condensation of biphenyl-2,6,2',6'-tetracarbaldehyde (6) and 2,2'-diaminobiphenyl (3) in benzene (TsOH catalyst) gave the tetra Schiff base 9,15,24,30-tetraazahexabenzo[d,f,jk,o,q,uv] dodecalene (4). 10,14,25,29-Tetraaza[d,f,jk,o,q,uv]dodecalene (5) was prepared analogously from 2,6,2',6,-tetraaminobiphenyl (7) and biphenyl-2,2'-dicarbaldehyde (2). The condensation of 6 with o-phenylenediamine and with 2,3-diaminonaphthalene afforded “hydride shift” products 10 and 13. The geometries of 4 and 5 are briefly discussed.",

author = "Mordecai Rabinovitz and Israel Agranat and Shaw, \{Wu Chang\}",

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T1 - Multiple Diamine-Dialdehyde Condensations. Synthesis of Heterocyclic Dodecalenes

AU - Rabinovitz, Mordecai

AU - Agranat, Israel

AU - Shaw, Wu Chang

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N2 - The diamine-dialdehyde condensation of biphenyl-2,6,2',6'-tetracarbaldehyde (6) and 2,2'-diaminobiphenyl (3) in benzene (TsOH catalyst) gave the tetra Schiff base 9,15,24,30-tetraazahexabenzo[d,f,jk,o,q,uv] dodecalene (4). 10,14,25,29-Tetraaza[d,f,jk,o,q,uv]dodecalene (5) was prepared analogously from 2,6,2',6,-tetraaminobiphenyl (7) and biphenyl-2,2'-dicarbaldehyde (2). The condensation of 6 with o-phenylenediamine and with 2,3-diaminonaphthalene afforded “hydride shift” products 10 and 13. The geometries of 4 and 5 are briefly discussed.

AB - The diamine-dialdehyde condensation of biphenyl-2,6,2',6'-tetracarbaldehyde (6) and 2,2'-diaminobiphenyl (3) in benzene (TsOH catalyst) gave the tetra Schiff base 9,15,24,30-tetraazahexabenzo[d,f,jk,o,q,uv] dodecalene (4). 10,14,25,29-Tetraaza[d,f,jk,o,q,uv]dodecalene (5) was prepared analogously from 2,6,2',6,-tetraaminobiphenyl (7) and biphenyl-2,2'-dicarbaldehyde (2). The condensation of 6 with o-phenylenediamine and with 2,3-diaminonaphthalene afforded “hydride shift” products 10 and 13. The geometries of 4 and 5 are briefly discussed.

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Multiple Diamine-Dialdehyde Condensations. Synthesis of Heterocyclic Dodecalenes

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