The Thermal Decomposition of Benzylidene-2-azidoanilines

Krbechek, L. O.; Takimoto, H. H.

doi:10.1021/jo01035a048

Search citation statements

Order By: Relevance

Paper Sections

Select...

Scheme 37 Proposed Mechanism For the Formation Of Quinoxalines1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1966

2010

Publication Types

Select...

Other5

Article2

Book1

Relationship

Self Cite0

Independent8

Authors

Journals

Cited by 21 publications

(9 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[7,239,250,251] Anils 56 derived from 2-azidoanilines cyclize on heating to 2-arylbenzimidazoles 57, with yields in the 48±96% range (Scheme 31). The filtrate was distilled in vacuo to remove solvent, P(OEt) 3 , and phosphate, and the residue was chromatographed (silica gel, Et 2 O).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Product Class 4: Benzimidazoles

Neier¹,

Bellus²

2002

Category 2, Hetarenes and Related Ring Systems

View full text Add to dashboard Cite

mentioning

confidence: 99%

“…Scheme 31 Thermolysis of Schiff Bases of 2-Azidoanilines [7,239,250,251] 58 is heated under reflux for a few minutes with iron and acetic acid, it is converted into the benzimidazol-2(3H)-one 59 in high yield (88%). [252] A number of other examples have been reported.…”

mentioning

confidence: 99%

Product Class 4: Benzimidazoles

Neier¹,

Bellus²

2002

Category 2, Hetarenes and Related Ring Systems

View full text Add to dashboard Cite

“…We now report on the successful cyclisation of the nitrogen analogues of these wayward carboxylic acid derivatives, namely the o-azidobenzimidate (6) and the o-azidobenzamidine (7), and on further examples of the cyclisation of the elusive o-azidobenzimidoyl chloride^. '^ The imidate (6) and the amidine hydrochloride (7) were prepared by standard procedures as outlined in Scheme 1.…”

mentioning

confidence: 99%

1H- and 2H-indazoles by thermal and photolytic decomposition of o-azidobenzoic acid and o-azidobenzaldehyde derivatives

ARDAKANI¹,

Smalley²,

Smith³

1983

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

Ethyl o-azidobenzimidate (6) and o-azidobenzamidine (7) on thermolysis yield 3-ethoxy-(9 ; X = OEt) and 3-amino-IH-indazole (9; X = NHJ, respectively. The former product is also obtained on irradiation of the imidate in methanol-tetrahydrofuran solution.2-Aryl-and 2heteroaryl-3-chloro-2H-indazoles have been prepared by the action of hot thionyl chloride on o-azidoanilides. The trichloro-2H-indazoles obtained by the action of phosphorus pentachloride on o-azidobenzanilide (1 2) and by the action of thionyl chloride on N-(0-azidobenzoyl) -2aminopyridine have been identified as the 3,5,7-trichloro derivatives. The reductive dehalogenation, nitration, and reactivity of the halogen towards nucleophiles, of 3-chloro-2-phenyl-2H-indazole (1 9) are reported.A new practicable synthesis of o-azidobenzaldehyde (31 ; X = 0) is described. Thermolysis of its phenyl hydrazone and semicarbazone derivatives yields 2H-indazoles.

show abstract

“…of water and allowed to stand for 15 hours. The solidified product was separated and recrystallized from benzene to yield 38 3. g. (76%) of white solid, m.p.…”

mentioning

confidence: 99%