FACILE SYNTHESIS OF MODEL INDAZOLO[2,1-c][1,3,4]BENZO-TRIAZEPINE-5,13-DIONES

In basic media, 2-aminobenzoic acids (5) react with 2-[N-(1-carboxyphenyl)]hydrazonoyl chlorides (6, 7) (precursors of the reactive nitrile imine 1,3-dipolar species) to afford good yields of the corresponding 2-[N'-(1-carboxyphenyl-2-amino)hydrazino]benzoic acids (8a-d, 9a). The latter acyclic...

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Published inHeterocycles Vol. 75; no. 12; pp. 2989 - 3004
Main Authors Zahra, Jalal A., El-Abadelah, Mustafa M., Abu Thaher, Bassam A., Laufer, Stefan, Boese, Roland
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.12.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Indazolo[2,1-c]benzotriazepine
HETEROCYCLES
Double Lactamization
X-Ray
M(2-Carboxyphenyl)hydrazonoyl Chloride
N-Arylamidrazone
DERIVATIVES
LONIDAMINE
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Abstract In basic media, 2-aminobenzoic acids (5) react with 2-[N-(1-carboxyphenyl)]hydrazonoyl chlorides (6, 7) (precursors of the reactive nitrile imine 1,3-dipolar species) to afford good yields of the corresponding 2-[N'-(1-carboxyphenyl-2-amino)hydrazino]benzoic acids (8a-d, 9a). The latter acyclic adducts, in the presence of 1,1'-carbonyldiimidazole (CDI), undergo two consecutive lactamizations involving both activated carboxyl groups and the suitably located hydrazino-NH partners, to deliver the respective indazolo[2,1-c]-[1,3,4]benzotriazepin- 5,13-diones (10a-d, 11a). Structural assignments for these novel tetracyclic products are based on analytical and spectral (IR, MS, NMR) data, and confirmed by single crystal X-ray structure determination for 10a.
AbstractList In basic media, 2-aminobenzoic acids (5) react with 2-[N-(1-carboxyphenyl)]hydrazonoyl chlorides (6, 7) (precursors of the reactive nitrile imine 1,3-dipolar species) to afford good yields of the corresponding 2-[N'-(1-carboxyphenyl-2-amino)hydrazino]benzoic acids (8a-d, 9a). The latter acyclic adducts, in the presence of 1,1'-carbonyldiimidazole (CDI), undergo two consecutive lactamizations involving both activated carboxyl groups and the suitably located hydrazino-NH partners, to deliver the respective indazolo[2,1-c]-[1,3,4]benzotriazepin- 5,13-diones (10a-d, 11a). Structural assignments for these novel tetracyclic products are based on analytical and spectral (IR, MS, NMR) data, and confirmed by single crystal X-ray structure determination for 10a.
Author Laufer, Stefan
Boese, Roland
El-Abadelah, Mustafa M.
Zahra, Jalal A.
Abu Thaher, Bassam A.
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  organization: Univ Duisburg Essen, Inst Anorgan Chem, D-45117 Essen, Germany
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Cites_doi 10.1007/s00706-006-0532-y
10.1016/j.ab.2005.06.015
10.1039/b301047c
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Keywords Indazolo[2,1-c]benzotriazepine
HETEROCYCLES
Double Lactamization
X-Ray
M(2-Carboxyphenyl)hydrazonoyl Chloride
N-Arylamidrazone
DERIVATIVES
LONIDAMINE
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Snippet In basic media, 2-aminobenzoic acids (5) react with 2-[N-(1-carboxyphenyl)]hydrazonoyl chlorides (6, 7) (precursors of the reactive nitrile imine 1,3-dipolar...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title FACILE SYNTHESIS OF MODEL INDAZOLO[2,1-c][1,3,4]BENZO-TRIAZEPINE-5,13-DIONES
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