Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

VOLUME 44 B

NUMBER  8

AUGUST 2005

CONTENTS

Rapid Communications

1641

First synthesis of (±)-tenuifolene and
ar-tenuifolene

IPC: Int.Cl.⁷ C 07 C

First total synthesis of the title compounds has been accomplished.

A Srikrishna* & B Beeraiah

Papers

1644

Preparation and characterization of cyclic-ketone derivatives of methyl undec-10-enoate and their cyclocondensation with mercaptoacetic acid

IPC: Int.Cl.⁷ C 07 C 49/11

Methyl undec-10-enoate reacts with cyclic ketones to give two products 3a, b and 4a, b. 3b and 4b on further condensation with mercaptoacetic acid afford spiro compounds.

Abdul Rauf* & Refat Jahan

1649

Microwave assisted Friedländer condensation: A comparative study of conventional versus microwave mediated solvent-free methodologies

IPC: Int.Cl.⁷ C 07 D 215/00

4-Arylquinolines have been prepared by Friedländer reaction with acid as a catalyst and without the catalyst under microwave assisted solvent-free conditions and compared with classical heating.

Y K Agrawal* & Hardik M Joshipura

1653

Syntheses of 1,3-disubstituted-5a-hydro­pyrrolo­[2,3-d]quinazolin[3,2-e]pyrimidin-6(5H)-ones: A comparison of conventional and microwave technique

IPC: Int.Cl.7 C 07 D

An exclusive new ring system of 1,3-disubstituted-5a-hydro­pyrrolo[2,3-d]quinazolino [3,2-e]pyrimidin-6(5H)-ones 4 has been synthesised from 4-chloro­pyrrolo[2,3-d]pyrimidines 2 which are prepared using phase transfer catalysts.

Cicily Augustine  & Y K Agrawal*

1659

Synthesis, X-ray diffraction study and biological activity of 7-hydroxy-4-methylquinolin-2(1H)-one

IPC: Int.Cl.⁷ C 07 D 215/00 // A 61 P 31/10, 31/04

7- Hydroxy - 4 - methylquinolin - 2(1H)- one (HMQ) has been synthesized by an easy and efficient microwave-assisted method. It has been characterized by spectral and X-ray differactometry studies.

M B Deshmukh, Savita Dhongade-Desai &

S S Chavan *

1663

Chemoselective reaction of indole 1,3-dicarboxy­lates towards hydrazine hydrate: Bisheterocycles: Synthesis and antimicrobial activity of some new 2-methyl-3-ethoxycarbonyl-1-oxadiazolyl/thiazo­lidi­no­nyl/pyrrolyl­aminocarbonylmethylindoles

IPC: Int.Cl.⁷ C 07 D 209/04

Manjunath G Bhovi  & Guru S Gadaginamath*

1669

Synthesis and anticancer activity studies on some 2-chloro-1,4-bis-(5-substituted-1,3,4-oxadiazol-2-ylmethyleneoxy) phenylene derivatives

IPC: Int.Cl.⁷ C 07 D 271/10 // A61 P 35/00

B Shivarama Holla*, K Narayana Poojary,

K Subrahmanya Bhat, Mithun Ashok &

Boja Poojary

1674

Synthesis and anti-inflammatory activity of 4-(5'-acetyl-6'-hydroxy-3'-methylbenzofuran-2'-yl)-cou­m­arin and 6-acetyl-3, 7-dimethyl-2-(coumarin-4'-yl) furo [3,2-g] chromen-5-one

IPC: Int.Cl.⁷ C 07 D 311/00 // A 61 P 29/00

Various 4-bromomethylcoumarins 1 have been reacted with diacetyl resorcinol 2 to afford corresponding ethers 3, which undergo intermolecular aldol condensation followed by dehydration to form 4-(5'-acetyl-6'-hydroxy-3'-methyl-benzofuran-2'-yl) coum­arin 4. Further, compound 4 on reaction with sodium acetate and acetic anhydride affords 6-acetyl-3,7-dimethyl-2-(coumarin-4'-yl) furo [3,2-g] chro­men-5-one 5. Their structures have been confirmed by IR, NMR and mass spectral data, of these compounds 4e, 4f and 5e show good anti-inflammatory and analgesic activity.

Manjunath Ghate* & Manohar V Kulkarni

1679

Some electrophilic substitution reactions on 1-substi­tuted-3-acetyl/carbethoxy-5-hydroxy-2-me­thyl­­indole and the antimicrobial activity of these new indole derivatives

IPC: Int.Cl.⁷ C 07 D 209/04 // 31/04, 31/10

Dundappa S Donawade &

Guru S Gadaginamath*

1686

Reaction of orthoesters with alcohols in the presence of acidic catalysts: A study

IPC: Int.Cl.⁷ C 07 C 31/00, C 07 C 69/00

H M Sampath Kumar*, Sipak Joyasawal,

B V S Reddy, P Pawan Chakravarthy,

A D Krishna & J S Yadav

1693

QSPR with TAU indices: Molar refractivity of diverse functional acyclic compounds

IPC: Int.Cl.⁷ C 07 C

Molar refractivity of diverse functional acyclic compounds (n = 166) has been correlated with first order TAU indices to unravel the diagnostic feature of the TAU scheme.

2-Methyl-4-penten-3-ol                     Reference alkane                          Normal alkane

Kunal Roy* & Achintya Saha

1708

Ab initio investigation of electrophilic addition of chlorine to norbornadiene

IPC: Int.Cl.⁷ C 07 C

The mechanism and stereochemistry of the addition of chlorine to norbonadiene have been investigated quantum chemically.

Exo                                                  endo

 

Rza Abbasoğlu

Notes

1713

Studies in the synthesis of bibenzyl

IPC: Int.Cl.⁷ C 07 C 15/12

Synthesis of bibenzyl by Friedel-Crafts reaction, Wurtz reaction, Wolff-Kishner reduction and by reduction of trans-stilbene is discussed.

S S Mahajan* & V A Kamath

1717

Synthesis of some new N-[5-methyl-1-(4-chloro­phenyl)-1,2,3-triazol-4-yl]carbamic acid ester derivatives

IPC: Int.Cl.⁷ C 07 D 249/04

The synthesis of some new N-[5-methyl-1-(4-chlorophenyl)-1,2,3-triazol-4-yl]carbamic acid ester derivatives has been reported.

Bin Quan, Shan-Xue Zhuang, Chun-Cheng Li & Heng-Shan Dong* 

1720

Reductive coupling of aromatic aldehydes to pinacols using active manganese under ultrasound irradiation

IPC: Int.Cl.⁷ C 07 C 47/228

The pinacol coupling of aromatic aldehydes has been carried out in 30-98% yield with active manganese at r.t. for 2 hr under ultrasound irradiation.

Yan-Jiang Bian*, Shu-Ming Liu, Ji-Tai Li & Tong- Shuang Li

1724

New heterocycles having double characters as antimicrobial and surface active agents:
Part 1 ¾ Nonionic compounds from fatty acid isothiocyanate

IPC: Int.Cl.⁷ C 07 D

The synthesis of nonionic surface active agents from long chain of fatty acid isothiocyanates 1a-c has been conceptualized and some model studies in that direction are reported.

M S Amine, A M F Eissa, A A El-Sawy,
A F Shaaban & R El- Sayed

1731

Kinetics of elimination reactions of cumyl chloride and its substituted derivatives in acetonitrile

IPC: Int.Cl.⁷ C 07 C // C 07 B 35/06

Dehydrochlorination of cumyl chloride in acetonitrile is reversible (A = B + C). Weak base pyridine prevents back addition of HCl and the reaction follows unimolecular mechanism. The rate of elimination is controlled by steric factors with electronic effect of α-substitiuent being unimportant.

S Balachandran* & D Santhosh Kumar

1735

Triterpenoids from Bignonia unguiscati roots

IPC: Int.Cl.⁷ A 61 K 35/00

Triterpenoids 1 and 2 have been isolated from Bignonia unguiscati roots and their structures are elucidated by spectroscopic and chemical methods.

1 R = H,  R¹ = OAc, R²= Me, R³ = COOH, R⁴ = OH

                                                                                    2 R = R¹ = OH, R² = COOH, R³ = Me, R⁴ = H

Biswanath Dinda*, Utpal Chandra De

Shiho Arimaa, Nariko Satoa &

Yoshihiro Harigayaa

1740

Anthraquinones from Artabotrys odoratissimus (Leaves)

IPC: Int.Cl.⁷ C 07 A 61 K 31/22

Two new anthraquinones have been isolated from the hexane extract of A.odoratissimus leaves and characteri­zed as 1- hydroxy -2, 5-dimethoxy -9,10- anthraquinone 1 and 1,4,5-trihydroxy-9,10-anthra­quinone 2 by spectral data.

Neelima Singh, Megha Sharma, Mustazi Jafri &

B K Mehta*

1742

Two new lipid constituents of Nigella sativa (Seeds)

IPC: Int.Cl.⁷ C 07 A 61 K 31/12, 31/045

Two new aliphatic compounds have been isolated from the n-hexane extract of N.sativa (seeds) and characterized as 16-triecosen-7-ol 1 and 6-non­ade­canone 2 by spectral and chemical means.

Neelima Singh, Manjul Verma, Darshana Mehta & B K Mehta*

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int. Cl.: International Classification, 7th Edition, 1999