TY - JOUR
T1 - Multiple Diamine-Dialdehyde Condensations. Synthesis of Heterocyclic Dodecalenes
AU - Rabinovitz, Mordecai
AU - Agranat, Israel
AU - Shaw, Wu Chang
PY - 1981/7
Y1 - 1981/7
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.
UR - http://www.scopus.com/inward/record.url?scp=0007386062&partnerID=8YFLogxK
U2 - 10.1021/jo00328a005
DO - 10.1021/jo00328a005
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AN - SCOPUS:0007386062
SN - 0022-3263
VL - 46
SP - 3018
EP - 3020
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 15
ER -