1,2,3,3a,4,9-Hexahydropyrrolo[2,1-b]quinazoline

Base Information

• Chemical Name: 1,2,3,3a,4,9-Hexahydropyrrolo[2,1-b]quinazoline
• CAS No.: 495-58-9
• Molecular Formula: C11H14N2
• Molecular Weight: 174.24226
• Mol file: 495-58-9.mol

Synonyms:1,2,3,3a,4,9-Hexahydropyrrolo[2,1-b]quinazoline;Dihydrodeoxypeganine

Chemical Property of 1,2,3,3a,4,9-Hexahydropyrrolo[2,1-b]quinazoline

Chemical Property:

• PSA: 15.27000
• LogP: 2.10990

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2,3,3a,4,9-Hexahydropyrrolo[2,1-b]quinazoline

There total 19 articles about 1,2,3,3a,4,9-Hexahydropyrrolo[2,1-b]quinazoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

pyrrolidine (123-75-1) + o-aminobenzaldehyde (529-23-7) → 1,2,3,3a,4,9-hexahydropyrrolo<2,1-b>quinazoline (495-58-9)

Guidance literature:

In butan-1-ol; at 200 ℃; for 0.5h; Time; Solvent; Mechanism; Microwave irradiation; Sealed tube;

DOI:10.1055/s-0033-1338852

Reference yield: 78.0%

carbon monoxide (201230-82-2) + 2-amino-N-(prop-2'-enyl)benzylamine (174536-44-8) → 1,2,3,3a,4,9-hexahydropyrrolo<2,1-b>quinazoline (495-58-9)

Guidance literature:

With hydrogen; triphenylphosphine; dirhodium tetraacetate; In ethyl acetate; at 80 ℃; for 20h; under 20685.9 Torr;

DOI:10.1071/CH9952023

Reference yield: 63.0%

pyrrolidine (123-75-1) + 2-nitro-benzaldehyde (552-89-6) → 1,2,3,3a,4,9-hexahydropyrrolo<2,1-b>quinazoline (495-58-9) + 2-(pyrrolidin-1-ylmethyl)benzenamine (55727-59-8)

Guidance literature:

With iron pentacarbonyl; In tetrahydrofuran; at -30 - 25 ℃; for 36h; Schlenk technique; Cooling with liquid nitrogen;

DOI:10.1021/acs.joc.0c00794

upstream raw materials:

2,3--3,4-dihydroquinazoline

carbon monoxide

2-amino-N-(prop-2'-enyl)benzylamine

2-nitro-N-(prop-2'-enyl)benzylamine

Downstream raw materials:

deoxyvasicinone

2-(pyrrolidin-1-ylmethyl)benzenamine

C₁₁H₁₂N₂O₂

deoxypeganine

Refernces

• 1、 Afanasyev, Oleg I.,Podyacheva, Evgeniya,Rudenko, Alexander,Tsygankov, Alexey A.,Makarova, Maria,Chusov, Denis. "Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family". . p. 9347 - 9360. Retrieved 2020/08/14.
• 2、 Dieckmann, Arne,Richers, Matthew T.,Platonova, Alena Yu.,Zhang, Chen,Seidel, Daniel,Houk. "Metal-free α-amination of secondary amines: Computational and experimental evidence for azaquinone methide and azomethine ylide intermediates". . p. 4132 - 4144. Retrieved 2013/06/04.