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Novel heterotricyclic systems: 2,6‐dioxa‐ and 2‐oxa‐6‐thia‐10‐azatricyclo‐[5.2.1.0 4,10 ] deeanes; 2,6‐dioxa‐11‐azatricyclo[5.3.1.0 4,11 ] undecane; and 9,13‐dioxa‐14‐azatetracyclo[6.5.1.0 2,7 .0 11,14 ]tetradeca‐2,4,6‐triene
Author(s) -
Broadbent H. Smith,
Burnham Weldon S.,
Sheeley Richard M.,
Olsen Richard K.
Publication year - 1976
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570130227
Subject(s) - chemistry , decane , substituent , condensation , bicyclic molecule , stereochemistry , medicinal chemistry , organic chemistry , physics , thermodynamics
The acid‐catalyzed condensation of 2‐amino‐1,3‐propanediols and 1,4‐diketones under water‐azeotroping conditions has led to the first synthesis of the new tent‐like, essentially strain‐free heterotricyclic system, 2,6‐dioxa‐10‐azatricyclo[5.2.1.0 4,10 ]decane. Over thirty new compounds containing this system are reported. In cases where the aminodiol is unsubstituted or bears a phenyl substituent a mixture of the tricycle and the isomeric pyrrole resulted. These observations indicate alternative pathways in the Knorr‐Paal condensation which lead to one, or the other, or both of these products. A scheme postulating common intermediates is presented. Examples of three additional, related, novel heteropolycyclic systems synthesized in analogous fashion are also reported.