4802-79-3

Basic information

• Product Name: 1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine
• Synonyms: 1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine;Indolo[2,3-a]quinolizidine;Indoloquinolizidine
• CAS NO: 4802-79-3
• Molecular Formula: C₁₅H₁₈N₂
• Molecular Weight: 226.3168
• Mol File: 4802-79-3.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 397.5°Cat760mmHg
• Flash Point: 194.2°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 1.58E-06mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: 1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine(4802-79-3)
• EPA Substance Registry System: 1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine(4802-79-3)

Safety Data

• Hazardous Substances Data: 4802-79-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 34, p. 3027, 1978 DOI: 10.1016/0040-4020(78)88027-2Tetrahedron Letters, 32, p. 161, 1991 DOI: 10.1016/0040-4039(91)80843-U

InChI:InChI=1/C15H18N2/c1-2-6-13-11(5-1)12-8-10-17-9-4-3-7-14(17)15(12)16-13/h1-2,5-6,14,16H,3-4,7-10H2

Upstream product

• 6940-78-9 4-chlorobutyl bromide 
• 10447-21-9 hexahydro-quinolizin-1-one 
• 100-63-0 phenylhydrazine 
• 5912-12-9 2,3,4,6,7,12-hexahydro-indolo[2,3-a]quinolizine 
• 3383-21-9 3,5-di-tert-butyl-o-benzoquinone 
• 136945-81-8 nazlinine 
• 6067-48-7 1,2,3,4,6,7-Hexahydro-12H-indolo<2.3-a>chinolizinium-chlorid 
• 21190-99-8 3-(dimethylaminomethyl)-2-(2-pyridyl)indole 
• 92437-52-0 2-(2-pyridyl)indole-3-acetic acid 
• 1122-62-9 2-acetylpyridine 
• 7734-05-6 2-acetylpyridine phenylhydrazone 
• 20862-83-3 2-(piperidin-2-yl)-1H-indole 
• 4942-85-2 1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-4-one 
• 86658-78-8 N-tosyl tryptamine 

Downstream Products

• 157069-66-4 6-benzyloxycarbonyl-1-methoxy-6-azacyclodeca<5,4-b>indole 
• 87960-40-5 cis-(H-1/H-12b)-1-benzoyloxy-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine 
• 157069-68-6 6-benzyloxycarbonyl-1-methoxyimino-6-azacyclodeca<5,4-b>indole 
• 157069-67-5 6-benzyloxycarbonyl-6-azacyclodeca<5,4-b>indol-1-one 
• 157069-69-7 6-benzyloxycarbonyl-6-azacyclodeca<5,4-b>indol-1-amine 

Relevant articles and documents

The Synthesis of (±)-1,2,3,4,6,7,12,12b-Octahydroindolo[2,3-a]quinolizine from Tryptophan and Dihydropyran

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A convenient synthesis of 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine

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A general strategy for the synthesis of indoloquinolizine alkaloids: Via a cyanide-catalyzed imino-Stetter reaction

A new strategy applicable to the synthesis of indoloquinolizine natural products has been developed. A cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines, derived from 2-aminocinnamic acid derivatives and 2-pyridinecarboxaldehydes, provided indole-3-acetic acid derivatives bearing a pyridyl ring at the 2-position. Reduction of the carboxylic acid moiety to an alcohol followed by activation of the resulting alcohol with Tf2O or TsCl generated indoloquinolizinium salts, which were utilized as precursors for indoloquinolizine natural products. The advantage of this protocol was successfully demonstrated in the total syntheses of arborescidine A and nauclefidine.

Tf2O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides

Ten types of Tf2O/TTBP-mediated amide transformation reactions were investigated. The results showed that compared with pyridine derivatives 2,6-di-tert-butyl-4-methylpyridine (DTBMP) and 2-fluoropyridine (2-F-Pyr.), TTBP can serve as an alternative amide activation system for the direct transformation of both secondary and tertiary amides. For most surveyed examples, higher or comparable yields were generally obtained. In addition, Tf2O/TTBP combination was used to promote the condensation reactions of 2-(tert-butyldimethylsilyloxy)furan (TBSOF) with both tertiary and secondary amides, the one-pot reductive Bischler-Napieralski-type reaction of tertiary lactams, and Movassaghi and Hill's modern version of the Bischler-Napieralski reaction. The value of the Tf2O/TTBP-based methodology was further demonstrated by the concise and high-yielding syntheses of several natural products.

One-pot tandem route to fused indolizidines and quinolizidines: Application in the synthesis of alkaloids and bioactive compounds

Fused indolizidines and quinolizidines are important skeletons in a variety of natural products and pharmacologically important compounds. A one-pot tandem route from amide to fused indolizidines and quinolizidines is disclosed. This method is conducted in mild conditions and shows well tolerance of functional groups. It is also easy to be scaled up to gram scale and can be applied smoothly to the total synthesis of alkaloids such as (±)-crispine A, (±)-xylopinine, (±)-desbromoarborescidine A, (±)-harmicine and other bioactive substances.